Isoxazoline-substituted benzamide compound and pesticide

ABSTRACT

A 3,5-Bis (substituted aryl) substituted isoxazoline compound of formula (2) or a salt thereof: 
     
       
         
         
             
             
         
       
     
     wherein A1 is a carbon atom or nitrogen atom; X1 is selected from the group consisting of a halogen atom, —SF5, C1-C6haloalkyl, hydroxy C1-C6haloalkyl, C1-C6alkoxy C1-C6haloalkyl, C1-C6haloalkoxy C1-C6haloalkyl, C3-C8halocycloalkyl, C1-C6haloalkoxy, C1-C3haloalkoxy C1-C3haloalkoxy, C1-C6haloalkylthio, C1-C6haloalkylsulfinyl and C1-C6haloalkylsulfonyl; X2 is selected from the group consisting of a halogen atom, cyano, nitro, C1-C6alkyl, C1-C6haloalkyl, —OR5, —OSO2R5 and —S(O)rR5; Y is selected from the group consisting of a halogen atom, cyano, nitro, C1-C4alkyl, C1-C4haloalkyl, C1-C4alkoxy, C1-C4haloalkoxy, C1-C6alkylthio, C1-C6haloalkylthio, C1-C6alkylsulfonyl, C1-C6haloalkylsulfonyl, —NHR7 and —N(R7)R6; R is selected from the group consisting of a halogen atom, cyano, nitro, —NH2, halosulfonyloxy, C1-C6alkylsulfonyloxy, C1-C6haloalkylsulfonyloxy, phenylsulfonyloxy, phenylsulfonyloxy substituted with (Z)p1 and —C(O)Ra; m1 is an integer of 0 to 2; n is an integer of 0 or 1; p1 is an integer of 1 to 5; and r is an integer of 0 to 2.

TECHNICAL FIELD

This is a Divisional Application of application Ser. No. 12/509,859,filed on Jul. 27, 2009, which is a Divisional Application of applicationSer. No. 11/514,921, filed Sep. 5, 2006, which in turn is aContinuation-in-part of International Application No. PCT/JP05/04268,filed Mar. 4, 2005, which claims priority to Japanese PatentApplications Nos. 2004-200119, filed Jul. 7, 2004, and 2004-061749,filed Mar. 5, 2004. The disclosures of the prior applications are herebyincorporated by reference herein in their entirety.

The present invention relates to a novel isoxazoline-substitutedbenzamide compound and the salt thereof, and a pesticide characterizedby containing the compound as an active ingredient. The pesticide in thepresent invention means a pest controlling agent applied for harmfularthropods in agricultural and horticultural field or livestock farmingand hygienic field (endo-parasiticides and ecto-parasiticides formammals or birds as domestic animals or pets, or hygienic pest- orunpleasant pest-controlling agents for domestic or business use). Inaddition, agricultural chemicals in the present invention meaninsecticides, acaricides (miticides), nematicides, herbicides andfungicides, and the like.

BACKGROUND ART

Conventionally, as to isoxazoline-substituted benzoic acid amidecompounds, the followings are known: a report of synthesis by use ofsolid phase synthesis of 4-(5-methyl-5-substitutedpyrrolyl-4,5-dihydroisoxazole-3-yl)benzoic acid amide derivatives (see,Non-patent Document 1); 4-(5-pyridyl-4,5-dihydroisoxazole-3-yl)benzoicacid amide derivatives have matrix metalloprotease and TNF-inhibitionactivity, or the like, and can be used as an anti-inflammatory agent ora chondro-protective agent (see, Patent Document 1); 4-(5-substitutedcarbamoylmethyl-4,5-dihydroisoxazole-3-yl)benzoic acid amidederivatives, 3-(5-substituted carbamoylmethyl-5-substitutedalkyl-4,5-dihydroisoxazole-3-yl)benzoic acid amide derivatives and4-(5-substituted carbamoylmethyl-4,5-dihydroisoxazole-3-yl)benzamidinederivatives have platelet glycoprotein IIb/IIIa fibrinogen receptorcomplex competitive activity or factor Xa inhibition activity or thelike, and can be used as a thrombolysis agent or a therapeutic agent ofthronbo-embolic disorder (see, for example Patent Documents 2-5), etc.In addition, it is known that other specific substituted isoxazolinecompound can be used as a production intermediate of HIV proteaseinhibitors, or production intermediate of insecticides (see, for examplePatent Documents 6 and 7). However, there is no disclosure on4-(5-substituted-5-substituted aryl-4,5-dihydroisoxazole-3-yl)benzoicacid amide compounds according to the present invention, and further theusefulness thereof as a pesticide is not known at all.

On the other hand, as to 3-(4-substituted phenyl)-4,5-dihydroisoxazolederivatives, 5-substituted alkyl-3,5-bis substitutedphenyl-4,5-dihydroisoxazole derivatives (see, Patent Document 7),3-alkoxyphenyl-5-substituted-5-phenyl-4,5-dihydroisoxazole derivatives(see, Patent Document 8), 3-alkoxyphenyl-5-substitutedalkyl-5-substituted carbamoyl-4,5-dihydroisoxazole derivatives (see,Patent Document 9), 3-(4-halophenyl)-5-substituted-5-substitutedphenyl-4,5-dihydroisoxazole derivatives (see, Patent Documents 10 andNon-patent Document 2), and3-(4-nitrophenyl)-5-substituted-5-substitutedphenyl-4,5-dihydroisoxazole derivatives (see, patent Document 11 andNon-patent Document 3), etc. are known. However, 5-substitutedalkyl-3,5-bis substituted phenyl-4,5-dihydroisoxazole derivatives thatcan be used as a production intermediate of the pesticides according tothe present invention are not described in any documents and thus novelcompounds.

Further, as to 4-hydroxyiminomethyl benzoic acid amide derivatives,4-hydroxyiminomethyl-N,N-dimethyl benzoic acid amide (see, Non-patentDocument 4), 4-hydroxyiminomethyl benzoyl piperidine derivatives (see,Patent Documents 12 and 13), 4-hydroxyiminomethyl-N-bicycloalkyl benzoicacid amide derivatives (see, Patent Document 14), and6-(hydroxyiminomethyl)pyridine-2-carboxamide derivatives (see,Non-patent Document 5), etc. are known. However, 4-hydroxyiminomethylbenzoic acid amide derivatives that can be used as a productionintermediate of the pesticides according to the present invention arenot described in any documents and thus novel compounds.

In addition, as to haloalkenylbenzene derivatives, substituted3,3,3-trifluoro-2-propenylbenzene derivatives (see, Non-patent Documents6-8), etc. are known. However, specific substituted haloalkenylbenzenederivatives that can be used as a production intermediate of thepesticides according to the present invention are not described in anydocuments and thus novel compounds.

-   Patent Document 1: WO 01/070673 Pamphlet-   Patent Document 2: WO 96/038426 Pamphlet-   Patent Document 3: WO 97/023212 Pamphlet-   Patent Document 4: WO 95/014683 Pamphlet-   Patent Document 5: WO 97/048395 Pamphlet-   Patent Document 6: WO 99/014210 Pamphlet-   Patent Document 7: WO 04/018410 Pamphlet-   Patent Document 8: WO 95/024398 Pamphlet-   Patent Document 9: WO 98/057937 Pamphlet-   Patent Document 10: EP 0455052 A1 (1991)-   Patent Document 11: WO 2004/018410 Pamphlet-   Patent Document 12: WO 95/019773 Pamphlet-   Patent Document 13: WO 00/066558 Pamphlet-   Patent Document 14: WO 97/000853 Pamphlet-   Non-patent Document 1: J. Comb. Chem., vol. 6, p. 142 (2004)-   Non-patent Document 2: Synth. Commun., vol. 33, p. 4163 (2003)-   Non-patent Document 3: Australian J. Chem., vol. 32, p. 1487 (1979)-   Non-patent Document 4: J. Chem. Soc. Perkin Trans, 1, p. 643 (1979)-   Non-patent Document 5: J. Org. Chem., vol. 35, p. 841 (1970)-   Non-patent Document 6: J. Org. Chem., vol. 24, p. 238 (1959)-   Non-patent Document 7: J. Am. Chem. Soc., vol. 101, p. 357 (1979)-   Non-patent Document 8: Bull. Chem. Soc. Jpn., vol. 69, p. 3273    (1996)

DISCLOSURE OF INVENTION Problems to be Solved by the Invention

Recently, pests acquire resistance by the use of pesticides such asinsecticides or fungicides over long term, and thus control by theinsecticides or fungicides that have been conventionally used becomesdifficult. In addition, a part of known pesticides has a high toxicity,or some of them start to disturb native ecosystems due to long-termpersistency. Under the circumstances, it is expected all the time todevelop a novel pesticide having a low toxicity and a low persistency.

Means for Solving the Problems

The inventors have eagerly investigated in order to solve theabove-mentioned problems, and as a result of it, they found that novelisoxazoline-substituted benzamide compounds of formula (1) are extremelyuseful compounds having excellent pest controlling activity,particularly insecticidal activity and acaricidal activity, and havinglittle adverse affect on non-targeted beings such as mammals, fishes anduseful insects, etc. Thus, the present invention has been accomplished.

That is, the present invention relates to the following aspects (1) to(15):

(1) An isoxazoline-substituted benzamide compound of formula (1) or asalt thereof:

wherein A¹, A¹ and A³ independently of one another are carbon atom ornitrogen atom,G is benzene ring, nitrogen-containing 6-membered aromatic heterocyclicring, furan ring, thiophene ring, or 5-membered aromatic heterocyclicring containing two or more hetero atoms selected from oxygen atom,sulfur atom and nitrogen atom,W is oxygen atom or sulfur atom,X is halogen atom, cyano, nitro, azido, —SCN, —SF₅, C₁-C₆alkyl,C₁-C₆alkyl arbitrarily substituted with R⁴, C₃-C₈cycloalkyl,C₃-C₈cycloalkyl arbitrarily substituted with R⁴, C₂-C₆alkenyl,C₂-C₆alkenyl arbitrarily substituted with R⁴, C₃-C₈cycloalkenyl,C₃-C₈halocycloalkenyl, C₂-C₆alkynyl, C₂-C₆alkynyl arbitrarilysubstituted with R⁴, —OH,—OR⁵, —OSO₂R⁵, —SH, —S(O)_(r)R⁵, —N═CHOR⁸, —N═C(R⁹)OR⁸, —CHO, —C(O)R⁹,—C(O)OR⁹, —C(O)SR⁹, —C(O)NHR¹⁰, —C(O)N(R¹⁰)R⁹, —C(S)OR⁹, —C(S)SR⁹,—C(S)NHR¹⁰, —C(S)N(R¹⁰)R⁹, —CH═NOR¹¹, —C(R⁹)═NOR¹¹, —S(O)₂OR⁹,—S(O)₂NHR¹⁰, —S(O)₂N(R¹⁰)R⁹, —Si(R¹³)(R¹⁴)R¹², phenyl, phenylsubstituted with (Z)_(p1), D-1 to D-65 or E-1 to E-49, when m is 2, 3, 4or 5, each X may be identical with or different from each other,further, when two Xs are adjacent, the adjacent two Xs may form5-membered or 6-membered ring together with carbon atoms to which thetwo Xs are bonded by forming —CH₂CH₂CH₂—, —CH₂CH₂O—, —CH₂OCH₂—, —OCH₂O—,—CH₂CH₂S—, —CH₂SCH₂—, —CH₂CH₂N(R¹⁵)—, —CH₂N(R¹⁵)CH₂—, —CH₂CH₂CH₂CH₂—,—CH₂CH₂CH₂O—, —CH₂CH₂OCH₂—, —CH₂OCH₂O—, —OCH₂CH₂O—, —OCH₂CH₂S—,—CH₂CH═CH—, —OCH═CH—, —SCH═CH—, —N(R¹⁵)CH═CH—, —OCH═N—, —SCH═N—,—N(R¹⁵)CH═N—, —N(R¹⁵)N═CH—, —CH═CHCH═CH—, —OCH₂CH═CH—, —N═CHCH═CH—,—N═CHCH═N— or —N═CHN═CH—, in this case, hydrogen atoms bonded to eachcarbon atom forming the ring may be arbitrarily substituted with Z,further when the hydrogen atoms are substituted with two or more Zs atthe same time, each Z may be identical with or different from eachother,Y is halogen atom, cyano, nitro, azido, —SCN, —SF₅, C₁-C₆alkyl,C₁-C₆alkyl arbitrarily substituted with R⁴, C₃-C₈cycloalkyl,C₃-C₈cycloalkyl arbitrarily substituted with R⁴, C₂-C₆alkynyl,C₂-C₆alkynyl arbitrarily substituted with R⁴, —OH, —OR⁵, —OSO₂R⁵, —SH,—S(O)_(r)R⁵, —NHR⁷, —N(R⁷)R⁶, —N═CHOR⁸, —N═C(R⁹)OR⁸, —C(O)NHR¹⁰,—C(O)N(R¹⁰)R⁹, —C(S)NHR¹⁰, —C(S)N(R¹⁰)R⁹, —Si(R¹³)(R¹⁴)R¹², phenyl,phenyl substituted with (Z)_(p1), D-1 to D-65 or E-1 to E-49, when n is2, 3 or 4, each Y may be identical with or different from each other,further, when two Ys are adjacent, the adjacent two Ys may form5-membered or 6-membered ring together with carbon atoms to which thetwo Ys are bonded by forming —CH₂CH₂CH₂—, —CH₂CH₂O—, —CH₂OCH₂—, —OCH₂O—,—CH₂CH₂S—, —CH₂SCH₂—, —SCH₂S—, —CH₂CH₂CH₂CH₂—, —CH₂CH₂CH₂O—,—CH₂CH₂OCH₂—, —CH₂OCH₂O—, —OCH₂CH₂O—, —OCH₂CH₂S—, —SCH₂CH₂S—, —OCH═N— or—SCH═N—, in this case, hydrogen atoms bonded to each carbon atom formingthe ring may be arbitrarily substituted with Z, further when thehydrogen atoms are substituted with two or more Zs at the same time,each Z may be identical with or different from each other, R¹ and R²independently of each other are hydrogen atom, cyano, C₁-C₁₂alkyl,C₁-C₁₂alkyl arbitrarily substituted with R¹⁶, C₃-C₁₂cycloalkyl,C₃-C₁₂cycloalkyl arbitrarily substituted with R¹⁶, C₂-C₁₂alkenyl,C₂-C₁₂alkenyl arbitrarily substituted with R¹⁶, C₃-C₁₂cycloalkenyl,C₃-C₁₂halocycloalkenyl, C₃-C₁₂alkynyl, C₃-C₁₂alkynyl arbitrarilysubstituted with R¹⁶, —SR⁹, —S(O)₂R⁹, —SN(R¹⁸)R¹⁷, —S(O)₂N(R¹⁰)R⁹,—OR¹⁹, —N(R²⁰)R¹⁹, —N═CHR^(19b), —N═C(R^(19b))R^(19a), —CHO, —C(O)R⁹,—C(O)OR⁹, —C(O)SR⁹, —C(O)N(R¹⁰)R⁹, —C(S)OR⁹, —C(S)SR⁹, —C(S)N(R¹⁰)R⁹,—C(═NR¹¹)OR⁹, —C(═NR¹¹)SR⁹, —C(═NR¹¹)N(R¹⁰)R⁹, phenyl, phenylsubstituted with (Z)_(p1), D-1 to D-63, D-65, E-3 to E-9, E17, E-23 toE-31, E-33, E-34 or E-45, or R¹ and R² together form ═C(R^(2a))R^(1a),or R¹ and R² together may form 3- to 8-membered ring together with thenitrogen atom bonding them by forming C₂-C₇ alkylene chain, in thiscase, the alkylene chain may contain one oxygen atom, sulfur atom ornitrogen atom, and may be arbitrarily substituted with halogen atom,C₁-C₆alkyl, C₁-C₆haloalkyl, C₁-C₆alkoxy (C₁-C₆)alkyl, C₁-C₆alkoxy,formyl, C₁-C₆alkylcarbonyl, C₁-C₆haloalkylcarbonyl, C₁-C₆alkoxycarbonyl,C₁-C₆haloalkoxycarbonyl, C₁-C₆alkylaminocarbonyl,C₁-C₆haloalkylaminocarbonyl, phenyl, phenyl substituted with (Z)_(p1),D-47, D-50, D-51, D-53 or 54,or in case where substituent Y is present at the adjacent position, R²together with Y may form 5- or 6-membered ring together with the atombonding them by forming —CH₂—, —CH₂CH₂—, —CH₂O—, —CH₂S—, —CH₂N(R⁶)—,—CH═CH— or —CH═N—, in this case, hydrogen atoms bonded to each carbonatom forming the ring may be arbitrarily substituted with halogen atom,C₁-C₆alkyl, C₁-C₆haloalkyl, C₁-C₆alkylidene, C₁-C₆haloalkylidene, oxo orthioxo,R^(1a) and R^(2a) together may form 5- or 6-membered ring together withthe carbon atom bonding them by forming C₄-C₅ alkylene chain or C₄-C₅alkenylene chain, in this case, the alkylene chain and the alkenylenechain may contain one to three oxygen atoms, sulfur atoms or nitrogenatoms, and may be arbitrarily substituted with halogen atom, C₁-C₆alkyl,C₁-C₆haloalkyl, C₁-C₆alkoxy, C₁-C₆haloalkoxy, C₁-C₆alkylthio orC₁-C₆haloalkylthio,R³ is halogen atom, cyano, C₁-C₆alkyl, C₁-C₆alkyl arbitrarilysubstituted with R⁴, C₃-C₈cycloalkyl, C₃-C₈cycloalkyl arbitrarilysubstituted with R⁴, C₃-C₆alkenyl, C₂-C₆alkenyl arbitrarily substitutedwith R⁴, C₃-C₆alkynyl, C₂-C₆alkynyl arbitrarily substituted with R⁴,—OR⁵, —S(O)_(r)R⁵, —N(R¹⁰)R⁹, —CHO, —C(O)R⁹, —C(O)OR⁹, —C(O)SR⁹,—C(O)NHR¹⁰, —C(O)N(R¹⁰)R⁹, —C(S)OR⁹, —C(S)SR⁹, —C(S)NHR¹⁰,—C(S)N(R¹⁰)R⁹,—CH═NOR¹¹, —C(R⁹)═NOR¹¹, —Si(R¹³)(R¹⁴)R¹², —P(O)(OR²¹)₂, phenyl, phenylsubstituted with (Z)_(p1), D-1 to D-65 or E-1 to E-49,D-1 to D-65 are aromatic heterocyclic rings of the following formulae,respectively

Z is halogen atom, cyano, nitro, C₁-C₆alkyl, C₁-C₆haloalkyl, C₁-C₄alkoxyC₁-C₄alkyl, C₁-C₄haloalkoxy C₁-C₄alkyl, C₁-C₄alkylthio C₁-C₄alkyl,C₁-C₄haloalkylthio C₁-C₄alkyl, C₁-C₄alkylsulfinyl C₁-C₄alkyl,C₁-C₄haloalkylsulfinyl C₁-C₄alkyl, C₁-C₄alkylsulfonyl C₁-C₄alkyl,C₁-C₄haloalkylsulfonyl C₁-C₄alkyl, C₃-C₆cycloalkyl, C₃-C₆halocycloalkyl,—OH, C₁-C₆alkoxy, C₁-C₆haloalkoxy, C₁-C₆alkylsulfonyloxy,C₁-C₆haloalkylsulfonyloxy, C₁-C₆alkylthio, C₁-C₆haloalkylthio,C₁-C₆alkylsulfinyl, C₁-C₆haloalkylsulfinyl, C₁-C₆alkylsulfonyl,C₁-C₆haloalkylsulfonyl, —NH₂, C₁-C₆alkylamino, di(C₁-C₆alkyl)amino,C₁-C₆alkoxycarbonyl, C₁-C₆haloalkoxycarbonyl, —C(O)NH₂,C₁-C₆alkylaminocarbonyl, C₁-C₆haloalkylaminocarbonyl,di(C₁-C₆alkyl)aminocarbonyl, —C(S)NH₂, —S(O)₂NH₂,C₁-C₆alkylaminosulfonyl, di(C₁-C₆alkyl)aminosulfonyl, phenyl or phenylarbitrarily substituted with halogen atom, when p1, p2, p3 or p4 is aninteger of 2 or more, each Z may be identical with or different fromeach other,further, when two Zs are adjacent, the adjacent two Zs may form5-membered or 6-membered ring together with carbon atoms to which thetwo Zs are bonded by forming —CH₂CH₂CH₂—, —CH₂CH₂O—, —CH₂OCH₂—, —OCH₂O—,—CH₂CH₂S—, —CH₂SCH₂—, —CH₂CH₂CH₂CH₂—, —CH₂CH₂CH₂O—, —CH₂CH₂OCH₂—,—CH₂OCH₂O—, —OCH₂CH₂O—, —CH₂CH₂CH₂S—, —OCH₂CH₂S— or —CH═CH—CH═CH—, inthis case, hydrogen atoms bonded to each carbon atom forming the ringmay be arbitrarily substituted with halogen atom, cyano, nitro,C₁-C₄alkyl, C₁-C₄haloalkyl, C₁-C₄alkoxy or C₁-C₄alkylthio,E-1 to E-49 are saturated heterocyclic rings of the following formulae,respectively

R⁴ is halogen atom, cyano, C₃-C₈cycloalkyl, C₃-C₈halocycloalkyl, —OH,—OR⁵, —SH, —S(O)_(r)R⁵, —N(R¹⁰)R⁹, —N(R¹⁰)CHO, —N(R¹⁰)C(O)R⁹,—N(R¹⁰)C(O)OR⁹,

—N(R¹⁰)C(O)SR⁹,

—N(R¹⁰)C(S)OR⁹, —N(R¹⁰)C(S)SR⁹, —N(R¹⁰)S(O)₂R⁹, —C(O)OR⁹, —C(O)N(R¹⁰)R⁹,—Si(R¹³)(R¹⁴)R¹², phenyl, phenyl substituted with (Z)_(p1), D-1 to D-65or E-1 to E-49, R⁵ is C₁-C₆alkyl, C₁-C₆alkyl arbitrarily substitutedwith R²⁴, C₃-C₈cycloalkyl, C₃-C₈cycloalkyl arbitrarily substituted withR²⁴, C₂-C₆alkenyl, C₂-C₆alkenyl arbitrarily substituted with R²⁴,C₃-C₈cycloalkenyl, C₃-C₈halocycloalkenyl, C₃-C₆alkynyl, C₃-C₆alkynylarbitrarily substituted with R²⁴, C₁-C₆alkylcarbonyl,C₁-C₆alkoxycarbonyl, phenyl, phenyl substituted with (Z)_(p1), D-1 toD-4, D-6 to D-13, D-15 to D-23, D-25 to D-37, D-39, D-40, D-42, D-45 toD-60, D-62, D-63, D-65, E-3 to E-9, E-23 to E-31, E-34 or E-45,R⁶ is C₁-C₆alkyl, C₁-C₆alkyl arbitrarily substituted with R²⁴,C₃-C₆cycloalkyl, C₃-C₈halocycloalkyl, C₃-C₆alkenyl, C₃-C₆haloalkenyl,C₃-C₆alkynyl, C₃-C₆haloalkynyl, —OH, C₁-C₆alkylcarbonyloxy,C₁-C₆alkylthio, C₁-C₆haloalkylthio, phenylthio, phenylthio substitutedwith (Z)_(p1),—SN(R¹⁸)R¹⁷, —S(O)₂R⁹, —S(O)₂N(R¹⁰)R⁹, —CHO, —C(O)R⁹, —C(O)OR⁹,—C(O)SR⁹, —C(O)NHR¹⁰, —C(O)N(R¹⁰)R⁹, —C(S)OR⁹, —C(S)SR⁹, —C(S)NHR¹⁰,—C(S)N(R¹⁰)R⁹, —C(O)C(O)R⁹, —C(O)C(O)OR⁹, —P(O)(OR²¹)₂ or —P(S)(OR²¹)₂,R⁷ is hydrogen atom, C₁-C₆alkyl, C₁-C₆haloalkyl, C₃-C₈cycloalkylC₁-C₆alkyl, C₁-C₄alkoxy C₁-C₄alkyl, C₁-C₄ alkylthio C₁-C₄alkyl,C₃-C₈cycloalkyl, C₃-C₆alkenyl, C₃-C₆haloalkenyl, C₃-C₆alkynyl,C₃-C₆haloalkynyl, —CHO, C₁-C₆alkylcarbonyl, C₁-C₆haloalkylcarbonyl orC₁-C₆alkoxycarbonyl, or R⁷ together with R⁶ may form 3- to 7-memberedring with the bonding nitrogen atom by forming C₂-C₆alkylene chain, inthis case, the alkylene chain may contain one oxygen atom, sulfur atomor nitrogen atom, and may be arbitrarily substituted with halogen atom,C₁-C₆alkyl, C₁-C₆haloalkyl, oxo or thioxo,R⁸ is C₁-C₆alkyl, C₁-C₆haloalkyl, C₃-C₆alkenyl, phenyl or phenylsubstituted with (Z)_(p1),R⁹ is C₁-C₆alkyl, C₁-C₆alkyl arbitrarily substituted with R²⁴,C₃-C₈cycloalkyl, C₃-C₈halocycloalkyl, C₂-C₆alkenyl, C₂-C₆haloalkenyl,C₂-C₆alkynyl, C₂-C₆haloalkynyl, phenyl, phenyl substituted with(Z)_(p1), D-1 to D-65 or E-1 to E-49, R¹⁰ is hydrogen atom, C₁-C₆alkyl,C₁-C₆haloalkyl, C₃-C₆cycloalkyl C₁-C₄alkyl, C₁-C₆alkoxy C₁-C₄alkyl,C₁-C₆alkylthio C₁-C₄alkyl, cyano C₁-C₆alkyl, C₃-C₆alkenyl orC₃-C₆alkynyl, R¹⁰ together with R⁹ may form 3- to 7-membered ring withthe atom bonding them by forming C₂-C₆alkylene chain, in this case, thealkylene chain may contain one oxygen atom, sulfur atom or nitrogenatom, and may be arbitrarily substituted with halogen atom, C₁-C₆alkylor C₁-C₆haloalkoxy, formyl, C₁-C₆alkylcarbonyl or C₁-C₆alkoxycarbonyl,R¹¹ is hydrogen atom, C₁-C₆alkyl, C₁-C₆haloalkyl, phenyl C₁-C₄alkyl,phenyl C₁-C₄alkyl substituted with (Z)_(p1), C₃-C₆alkenyl,C₃-C₆haloalkenyl, C₃-C₆alkynyl, C₃-C₆haloalkynyl, phenyl or phenyl thatmay be substituted with (Z)_(p1), R¹¹ together with R⁹ may form 5- to7-membered ring with the atom bonding them by forming C₂-C₄alkylenechain, in this case, the alkylene chain may contain one oxygen atom,sulfur atom or nitrogen atom, and may be arbitrarily substituted withhalogen atom, C₁-C₆alkyl or C₁-C₆haloalkyl,R¹² is C₁-C₆alkyl, C₁-C₆haloalkyl, phenyl or phenyl substituted with(Z)_(p1),R¹³ and R¹⁴ independently of each other are C₁-C₆alkyl orC₁-C₆haloalkyl,R¹⁵ is hydrogen atom, C₁-C₆alkyl, C₁-C₆haloalkyl, C₁-C₆alkoxycarbonylC₁-C₄alkyl, C₁-C₆haloalkoxycarbonyl C₁-C₄alkyl, phenyl C₁-C₄alkyl,phenyl C₁-C₄alkyl substituted with (Z)_(p1), C₃-C₆alkenyl,C₃-C₆haloalkenyl, C₃-C₆alkynyl, C₃-C₆haloalkynyl, C₁-C₆alkoxy,C₁-C₆alkoxycarbonyl, C₁-C₆haloalkoxycarbonyl, phenyl or phenylsubstituted with (Z)_(p1),further, in case where Z is present in an adjacent position of R¹⁵, theadjacent R¹⁵ and Z may form 6-membered ring together with the atombonding them by forming —CH₂CH₂CH₂CH₂—, —CH═CH—CH═CH—, —N═CH—CH═CH—,—CH═N—CH═CH—, —CH═CH—N═CH— or —CH═CH—CH═N—, in this case, hydrogen atomsbonded to each carbon atom forming the ring may be arbitrarilysubstituted with halogen atom, C₁-C₄alkyl or C₁-C₄haloalkyl,R¹⁶ is halogen atom, cyano, nitro, C₃-C₈cycloalkyl, C₃-C₈halocycloalkyl,hydroxy C₃-C₆cycloalkyl, C₁-C₄alkoxy C₃-C₆cycloalkyl, C₅-C₆cycloalkenyl,—OR²⁵, —N(R²⁶)R²⁵, —SH, —S(O)_(r)R²⁷, —SO₂OH, —SO₂NHR²⁹, —SO₂N(R²⁹)R²⁸,—CHO, —C(O)R²⁸, —C(O)OH, —C(O)OR²⁸, —C(O)SR²⁸, —C(O)NHR²⁹,—C(O)N(R²⁹)R²⁸, —C(O)N(R²⁹)OR²⁸, —C(O)N(R²⁹)N(R^(28a))R²⁸, —C(S)OR²⁸,—C(S)SR²⁸, —C(S)NHR²⁹, —C(S)N(R²⁹)R²⁸, —C(O)C(O)OR²⁸, —C(R³¹)═NOH,—C(R³¹)═NOR³⁰, —C(═NR³¹)OR³⁰, —C(═NR³¹)SR³⁰, —C(═NR³¹)N(R²⁹)R³⁰,—C(═NOR³¹)NHR²⁹, —C(═NOR³¹)N(R²⁹)R³⁰, —Si(R¹³)(R¹⁴)R¹², —P(O)(OR²¹)₂,—P(S)(OR²¹)₂, —P(phenyl)₂, —P(O)(phenyl)₂, phenyl, phenyl substitutedwith (Z)_(p1), naphthyl, D-1 to D-65, E-1 to E-49 or M-1 to M-22,M-1 to M-22 are partially saturated heterocyclic rings of the followingformulae, respectively

R¹⁷ is C₁-C₁₂alkyl, C₁-C₁₂haloalkyl, C₁-C₁₂alkoxy C₁-C₁₂alkyl, cyanoC₁-C₁₂alkyl, C₁-C₁₂alkoxycarbonyl C₁-C₁₂alkyl, phenyl C₁-C₄alkyl, phenylC₁-C₄alkyl substituted with (Z)_(p1), C₃-C₁₂alkenyl, C₃-C₁₂haloalkenyl,C₃-C₁₂alkynyl, C₃-C₁₂haloalkynyl, C₁-C₁₂alkylcarbonyl,C₁-C₁₂alkoxycarbonyl, —C(O)ON═C(CH₃)SCH₃, —C(O)ON═C(SCH₃)C(O)N(CH₃)₂,phenyl or phenyl substituted with (Z)_(p1),R¹⁸ is C₁-C₁₂alkyl, C₁-C₁₂haloalkyl, C₁-C₁₂alkoxy C₁-C₁₂alkyl, cyanoC₁-C₁₂alkyl, C₁-C₁₂alkoxycarbonyl C₁-C₁₂alkyl, phenyl C₁-C₄alkyl, phenylC₁-C₄alkyl substituted with (Z)_(p1), C₃-C₁₂alkenyl, C₃-C₁₂haloalkenyl,C₃-C₁₂alkynyl, C₃-C₁₂haloalkynyl, phenyl or phenyl substituted with(Z)_(p1), or R¹⁸ together with R¹⁷ may form 5- to 8-membered ring withthe nitrogen atom bonding them by forming C₄-C₇alkylene chain, in thiscase, the alkylene chain may contain one oxygen atom or sulfur atom, andmay be arbitrarily substituted with C₁-C₄alkyl or C₁-C₄alkoxy,R¹⁹ is hydrogen atom, C₁-C₆alkyl, C₁-C₆alkyl arbitrarily substitutedwith R¹⁶, C₃-C₈cycloalkyl, C₃-C₈halocycloalkyl, C₃-C₆alkenyl,C₃-C₆haloalkenyl, C₃-C₆alkynyl, C₃-C₆haloalkynyl, —CHO, —C(O)R²⁸,—C(O)OR²⁸, —C(O)SR²⁸, —C(O)NHR²⁹, —C(O)N(R²⁹)R²⁸, —C(S)OR²⁸, —C(S)SR²⁸,—C(S)NHR²⁹, —C(S)N(R²⁹)R²⁸, —S(O)₂R²⁸, —S(O)₂NHR²⁹, —S(O)₂N(R²⁹)R²⁸,—P(O)(OR²¹)₂, —P(S)(OR²¹)₂, phenyl, phenyl substituted with (Z)_(p1),D-1 to D-13, D-15 to D-25, D-30 to D-37, D-39, D-40, D-42, D-45 to D-60,E-5, E-7, E-9, E-24, E-25, E-27, E-28, E-30 or E-31,R^(19a) is hydrogen atom, C₁-C₆alkyl, C₁-C₆haloalkyl, C₁-C₄alkoxyC₁-C₄alkyl, C₁-C₄alkylthio C₁-C₄alkyl, C₁-C₄alkylsulfonyl C₁-C₄alkyl,C₁-C₄alkoxycarbonyl C₁-C₄alkyl, phenyl C₁-C₄alkyl, phenyl C₁-C₄alkylsubstituted with (Z)_(p1), C₃-C₆cycloalkyl, phenyl C₂-C₄alkenyl,di(C₁-C₆alkyl)amino, phenyl, phenyl substituted with (Z)_(p1), D-1 toD-65 or E-1 to E-49,R^(19b) is hydrogen atom, C₁-C₆alkyl, C₁-C₆alkoxy, C₁-C₆alkylthio ordi(C₁-C₆alkyl)amino, or R^(19a) together with R^(19b) may form 4- to6-membered ring with the carbon atom bonding them by formingC₃-C₅alkylene chain, in this case, the alkylene chain may contain oneoxygen atom, sulfur atom or nitrogen atom, and may be arbitrarilysubstituted with halogen atom, C₁-C₆alkyl, C₁-C₆haloalkyl, formyl,C₁-C₆alkylcarbonyl or C₁-C₆alkoxycarbonyl,R²⁰ is hydrogen atom, C₁-C₆alkyl, C₁-C₆haloalkyl, C₁-C₄alkoxyC₁-C₄alkyl, C₁-C₄haloalkoxy C₁-C₄alkyl, C₁-C₄alkylthio C₁-C₄alkyl,C₁-C₄haloalkylthio C₁-C₄alkyl, C₁-C₄alkylsulfonyl C₁-C₄alkyl,C₁-C₄haloalkylsulfonyl C₁-C₄alkyl, cyano C₁-C₆alkyl, C₁-C₄alkoxycarbonylC₁-C₄alkyl, phenyl C₁-C₄alkyl, C₂-C₆alkenyl, C₂-C₆haloalkenyl,C₃-C₆alkynyl, C₃-C₆haloalkynyl, —CHO, —C(O)R⁹, —C(O)OR⁹, —C(O)SR⁹,—C(S)OR⁹, —C(S)SR⁹, C₁-C₆alkylsulfonyl or C₁-C₆haloalkylsulfonyl, or R²⁰together with R¹⁹ may form 5- to 6-membered ring with the nitrogen atombonding them by forming C₄-C₅alkylene chain, in this case, the alkylenechain may contain one oxygen atom, sulfur atom or nitrogen atom, and maybe arbitrarily substituted with C₁-C₆alkyl, C₁-C₆alkoxy C₁-C₆alkyl,—CHO, C₁-C₆alkylcarbonyl or C₁-C₆alkoxycarbonyl,R²¹ is C₁-C₆alkyl or C₁-C₆haloalkyl,R²² is halogen atom, cyano, C₁-C₆alkyl, C₁-C₆haloalkyl, hydroxyC₁-C₆alkyl, C₁-C₄alkoxy C₁-C₄alkyl, C₁-C₄alkoxycarbonyl C₁-C₄alkyl,C₁-C₆alkoxy, C₁-C₆alkylthio, C₁-C₆alkylamino, di(C₁-C₄alkyl)amino,C₁-C₆alkoxycarbonyl, phenyl or phenyl substituted with (Z)_(p1), whenq1, q2, q3 or q4 is an integer of 2 or more, each R²² may be identicalwith or different from each other, further in case where two R²²s arepresent on the same carbon atom, the two R²²s together may form oxo,thioxo, imino, C₁-C₆alkylimino, C₁-C₆alkoxyimino or C₁-C₆alkylidene,R²³ is hydrogen atom, C₁-C₆alkyl, C₁-C₆alkyl substituted with R³²,C₃-C₆cycloalkyl, C₃-C₆alkenyl, C₃-C₆haloalkenyl, C₃-C₆alkynyl, —OH,benzyloxy, —CHO, —C(O)R³³, —C(O)OR³³, —C(O)SR³³, —C(O)NHR³⁴,—C(O)N(R³⁴)R³³, —C(S)NHR³⁴, —C(S)N(R³⁴)R³³, —S(O)₂R³³, —P(O)(OR²¹)₂,—P(S)(OR²¹)₂, phenyl, phenyl substituted with (Z)_(p1) or D-5,R²⁴ is halogen atom, cyano, C₃-C₈cycloalkyl, C₃-C₈halocycloalkyl,C₁-C₆alkoxy, C₁-C₆haloalkoxy, C₁-C₆alkylthio, C₁-C₆haloalkylthio,C₁-C₆alkylsulfonyl, C₁-C₆haloalkylsulfonyl, C₁-C₆alkylamino,di(C₁-C₆alkyl)amino, —CHO, C₁-C₆alkylcarbonyl, C₁-C₆haloalkylcarbonyl,C₁-C₆alkoxycarbonyl, C₁-C₆haloalkoxycarbonyl, C₁-C₆alkylaminocarbonyl,di(C₁-C₆alkyl)aminocarbonyl, phenyl, phenyl substituted with (Z)_(p1),D-1 to D-65 or E-1 to E-49,R²⁵ is hydrogen atom, C₁-C₈alkyl, C₁-C₈alkyl arbitrarily substitutedwith R³², C₃-C₈cycloalkyl, C₃-C₈cycloalkyl arbitrarily substituted withR³², C₃-C₈alkenyl, C₃-C₈alkenyl arbitrarily substituted with R³²,C₃-C₈alkynyl, C₃-C₈alkynyl arbitrarily substituted with R³², —CHO,—C(O)R³³, —C(O)OR³³, —C(O)SR³³, —C(O)NHR³⁴, —C(O)N(R³⁴)R³³,—C(O)C(O)R³³, —C(O)C(O)OR³³, —C(S)R³³, —C(S)OR³³, —C(S)SR³³, —C(S)NHR³⁴,—C(S)N(R³⁴)R³³, —S(O)₂R³³, —S(O)₂N(R³⁴)R³³, —Si(R¹³)(R¹⁴)R¹²,—P(O)(OR²¹)₂, —P(S)(OR²¹)₂, phenyl, phenyl substituted with (Z)_(p1),D-1 to D-4, D-6 to D-13, D-15 to D-23, D-25 to D-37, D-39, D-40, D-42,D-45 to D-60, D-62, D-63, D-65, E-3 to E-9, E-23 to E-31, E-34 or E-45,R²⁶ is hydrogen atom, C₁-C₆alkyl, C₁-C₆haloalkyl, C₁-C₄alkoxyC₁-C₄alkyl, C₁-C₄alkylthio C₁-C₄alkyl, C₃-C₆cycloalkyl, C₃-C₆alkenyl,C₃-C₆alkynyl, C₁-C₆alkoxy, phenyl or phenyl substituted with (Z)_(p1),or R²⁶ together with R²⁵ may form 3- to 6-membered ring with thenitrogen atom bonding them by forming C₂-C₅alkylene chain, in this case,the alkylene chain may contain one oxygen atom, sulfur atom or nitrogenatom, and may be substituted with halogen atom, C₁-C₆alkyl,C₁-C₆haloalkyl, C₁-C₆alkoxy, phenyl, phenyl substituted with (Z)_(p1),oxo or thioxo,R²⁷ is C₁-C₈alkyl, C₁-C₈alkyl arbitrarily substituted with R³²,C₃-C₈cycloalkyl, C₃-C₈cycloalkyl arbitrarily substituted with R³²,C₃-C₈alkenyl, C₃-C₈alkenyl arbitrarily substituted with R³²,C₃-C₈alkynyl, C₃-C₈alkynyl arbitrarily substituted with R³², —SH,C₁-C₆alkylthio, C₁-C₆haloalkylthio, phenylthio, phenylthio substitutedwith (Z)_(p1), —CHO, —C(O)R³³, —C(O)OR³³, —C(O)SR³³, —C(O)NHR³⁴,—C(O)N(R³⁴)R³³, —C(O)C(O)R³³, —C(O)C(O)OR³³, —C(S)R³³, —C(S)OR³³,—C(S)SR³³, —C(S)NHR³⁴, —C(S)N(R³⁴)R³³,—P(O)(OR²¹)₂, —P(S)(OR²¹)₂, phenyl, phenyl substituted with (Z)_(p1),D-18, D-21, D-25, D-30 to D-35, D-47, D-50, D-51, E-3 to E-9, E-23 toE-31, E-34 or E-45,R²⁸ is C₁-C₆alkyl, C₁-C₆alkyl arbitrarily substituted with R³²,C₃-C₈cycloalkyl, C₃-C₈cycloalkyl arbitrarily substituted with R³²,C₂-C₆alkenyl C₃-C₈cycloalkyl, C₂-C₆haloalkenyl C₃-C₈cycloalkyl,C₂-C₈alkenyl, C₂-C₈alkenyl arbitrarily substituted withR³², C₂-C₈alkynyl, C₂-C₈alkynyl arbitrarily substituted with R³²,phenyl, phenyl substituted with (Z)_(p1), D-1 to D-65 or E-1 to E-49,R^(28a) is hydrogen atom or C₁-C₆alkyl,R²⁹ is hydrogen atom, C₁-C₆alkyl, C₁-C₆alkyl arbitrarily substitutedwith R³², C₃-C₆alkenyl, C₃-C₆haloalkenyl, C₃-C₆alkynyl,C₃-C₆haloalkynyl, phenyl or phenyl substituted with (Z)_(p1), or R²⁹together with R²⁸ may form 3- to 6-membered ring with the nitrogen atombonding them by forming C₂-C₅alkylene chain, in this case, the alkylenechain may contain one oxygen atom, sulfur atom or nitrogen atom, and maybe arbitrarily substituted with halogen atom, C₁-C₆alkyl, C₁-C₆alkoxy,formyl, C₁-C₆alkylcarbonyl, C₁-C₆alkoxycarbonyl, phenyl or phenylsubstituted with (Z)_(p1),R³⁹ is C₁-C₈alkyl, C₁-C₈alkyl arbitrarily substituted with R³²,C₃-C₈cycloalkyl, C₃-C₈alkenyl, C₃-C₈alkenyl arbitrarily substituted withR³², C₃-C₈alkynyl, C₃-C₈alkynyl arbitrarily substituted with R³²,R³¹ is hydrogen atom, C₁-C₆alkyl, C₁-C₆haloalkyl, C₃-C₆cycloalkylC₁-C₄alkyl, C₁-C₆alkoxy C₁-C₄alkyl, C₁-C₆haloalkoxy C₁-C₄alkyl,C₁-C₆alkylthio C₁-C₄alkyl, C₁-C₆haloalkylthio C₁-C₄alkyl,C₁-C₆alkylsulfonyl C₁-C₄alkyl, C₁-C₆haloalkylsulfonyl C₁-C₄alkyl, phenylC₁-C₄alkyl, phenyl C₁-C₄alkyl substituted with (Z)_(pt) C₃-C₆cycloalkyl,phenyl or phenyl substituted with (Z)_(p1), or R³¹ together with R³⁹ mayform 5- to 7-membered ring with the atom bonding them by formingC₂-C₄alkylene chain, in this case, the alkylene chain may contain oneoxygen atom, sulfur atom or nitrogen atom, and may be arbitrarilysubstituted with halogen atom, C₁-C₆alkyl or C₁-C₆haloalkyl,R³² is halogen atom, cyano, nitro, C₃-C₈cycloalkyl, C₃-C₈halocycloalkyl,—OH, —OR³³, —OC(O)R³³, —OC(O)OR³³, —OC(O)NHR³⁴, —OC(O)N(R³⁴)R³³,—OC(S)NHR³⁴, —OC(S)N(R³⁴)R³³, —SH, —S(O)_(r)R³³, —SC(O)R³³, —SC(O)OR³³,—SC(O)NHR³⁴, —SC(O)N(R³⁴)R³³, —SC(S)NHR³⁴, —SC(S)N(R³⁴)R³³, —NHR³⁴,—N(R³⁴)R³³, —N(R³⁴)CHO, —N(R³⁴)C(O)R³³, —N(R³⁴)C(O)OR³³,—N(R³⁴)C(O)NHR³⁴, —N(R³⁴)C(O)N(R³⁴)R³³, —N(R³⁴)C(S)NHR³⁴,—N(R³⁴)C(S)N(R³⁴)R³³, —CHO, —C(O)R³³, —C(O)OR³³, —C(O)SR³³, —C(O)NHR³⁴,—C(O)N(R³⁴)R³³, —C(O)C(O)OR³³, —Si(R¹³)(R¹⁴)R¹², —P(O)(OR²¹)₂,—P(S)(OR²¹)₂, —P(phenyl)₂, —P(O)(phenyl)₂, phenyl, phenyl substitutedwith (Z)_(p1), D-1 to D-65 or E-4 to E-7, E10 to E-14, E-18, E-19, E-23to E-28, E-32 to E-38, E-43, E-44 or E-45,R³³ is C₁-C₆alkyl, C₁-C₆haloalkyl, C₁-C₄alkyl arbitrarily substitutedwith R³⁵, C₃-C₆cycloalkyl, C₃-C₆halocycloalkyl, C₂-C₆alkenylC₃-C₈cycloalkyl, C₂-C₆haloalkenyl C₃-C₈cycloalkyl, C₂-C₈alkenyl,C₂-C₈haloalkenyl, C₃-C₈cycloalkenyl, C₃-C₈halocycloalkenyl,C₂-C₈alkynyl, C₂-C₈haloalkynyl, phenyl, phenyl substituted with(Z)_(p1), D-1 to D-65, E-4 to E-7, E-23 to E-27 or E-28,R³⁴ is hydrogen atom, C₁-C₆alkyl, C₁-C₆haloalkyl, C₃-C₈cycloalkyl,C₃-C₆alkenyl, C₃-C₆alkynyl, C₁-C₆alkylcarbonyl, C₁-C₆haloalkylcarbonyl,C₁-C₆alkoxycarbonyl, C₁-C₆haloalkoxycarbonyl, phenoxycarbonyl,phenoxycarbonyl substituted with (Z)_(p1), phenylcarbonyl,phenylcarbonyl substituted with (Z)_(p1), C₁-C₆alkylsulfonyl,C₁-C₆haloalkylsulfonyl, phenyl, phenyl substituted with (Z)_(p1), D-1 toD-4, D-6 to D-13, D-15 to D-23, D-25 to D-37, D-39, D-40, D-42, D-45 toD-60, D-62, D-63 or D-65, or R³⁴ together with R³³ may form 3- to6-membered ring with the nitrogen atom bonding them by formingC₂-C₅alkylene chain, in this case, the alkylene chain may contain oneoxygen atom, sulfur atom or nitrogen atom, and may be arbitrarilysubstituted with halogen atom, C₁-C₆alkyl, C₁-C₆alkoxy, formyl,C₁-C₆alkylcarbonyl, C₁-C₆alkoxycarbonyl, phenyl or phenyl substitutedwith (Z)_(p1),R³⁵ is cyano, C₃-C₆cycloalkyl, C₃-C₆halocylcoalkyl, E-4 to E-7, E-23 toE-28, C₁-C₄alkoxy, C₁-C₄haloalkoxy, C₁-C₄alkylthio, C₁-C₄haloalkylthio,C₁-C₄alkylsulfonyl, C₁-C₄haloalkylsulfonyl, C₁-C₆alkylcarbonyl,C₁-C₆haloalkylcarbonyl, C₁-C₆alkoxycarbonyl,di(C₁-C₆alkyl)aminocarbonyl, tri(C₁-C₆alkyl)silyl, phenyl, phenylsubstituted with (Z)_(p1) or D-1 to D-65,m is an integer of 0 to 5,n is an integer of 0 to 4,p1 is an integer of 1 to 5,p2 is an integer of 0 to 4,p3 is an integer of 0 to 3,p4 is an integer of 0 to 2,p5 is an integer of 0 or 1,q1 is an integer of 0 to 3,q2 is an integer of 0 to 5,q3 is an integer of 0 to 7,q4 is an integer of 0 to 9,r is an integer of 0 to 2, andt is an integer of 0 or 1.(2) The isoxazoline-substituted benzamide compound or the salt thereofas set forth in (1), whereinG is an aromatic 6-membered ring shown in any one of G-1 to G-10 or anaromatic 5-membered ring shown in any one of G-11 to G-25

X is halogen atom, cyano, nitro, —SF₅, C₁-C₆alkyl, C₁-C₆alkylarbitrarily substituted with R⁴, C₃-C₈cycloalkyl, C₃-C₈cycloalkylarbitrarily substituted with R⁴, C₂-C₆alkenyl, C₂-C₆alkenyl arbitrarilysubstituted with R⁴, C₂-C₆alkynyl, C₂-C₆alkynyl arbitrarily substitutedwith R⁴,

—OH, —OR⁵, —OSO₂R⁵, —S(O)_(r)R⁵, —C(O)OR⁹, —C(O)SR⁹,

—C(O)NHR¹⁰, —C(O)N(R¹⁰)R⁹, —C(S)OR⁹, —C(S)SR⁹, —C(S)NHR¹⁰,—C(S)N(R¹⁰)R⁹, —CH═NOR¹¹, —C(R⁹)═NOR¹¹, —S(O)₂NHR¹⁰, —S(O)₂N(R¹⁰)R⁹,—Si(R¹³)(R¹⁴)R¹², phenyl, phenyl substituted with (Z)_(p1), D-1 to D-60or E-1 to E-49, when m is an integer of 2 or more, each X may beidentical with or different from each other,further, when two Xs are adjacent, the adjacent two Xs may form5-membered or 6-membered ring together with carbon atoms to which thetwo Xs are bonded by forming—CH₂CH₂CH₂—, —CH₂CH₂O—, —CH₂OCH₂—, —OCH₂O—, —CH₂CH₂S—, —CH₂SCH₂—,—CH₂CH₂CH₂CH₂—, —CH₂CH₂CH₂O—, —CH₂CH₂OCH₂—, —CH₂OCH₂O—, —OCH₂CH₂O—,—OCH₂CH₂S— or —CH═CHCH═CH—, in this case, hydrogen atoms bonded to eachcarbon atom forming the ring may be arbitrarily substituted with halogenatom, C₁-C₄alkyl or C₁-C₄haloalkyl,Y is halogen atom, cyano, nitro, C₁-C₆alkyl, C₁-C₆alkyl arbitrarilysubstituted with R⁴, —OR⁵, —OSO₂R⁵, —S(O)_(r)R⁵, —NHR⁷, —N(R⁷)R⁶,—N═CHOR⁸, —N═C(R⁹)OR⁸, —C(O)NHR¹⁰,—C(O)N(R¹⁰)R⁹, —C(S)NHR¹⁰, —C(S)N(R¹⁰)R⁹, phenyl, phenyl substitutedwith (Z)_(p1), D-1 to D-24, D-30 to D-38, D-43 to D-52 or D-53, when nis an integer of 2 or more, each Y may be identical with or differentfrom each other,further, when two Ys are adjacent, the adjacent two Ys may form5-membered or 6-membered ring together with carbon atoms to which thetwo Ys are bonded by forming—CH₂CH₂CH₂—, —CH₂CH₂O—, —CH₂OCH₂—, —OCH₂O—, —CH₂CH₂CH₂CH₂—,—CH₂CH₂CH₂O—, —CH₂CH₂OCH₂—, —CH₂OCH₂O—, —OCH₂CH₂O—, —OCH═N— or —SCH═N—,in this case, hydrogen atoms bonded to each carbon atom forming the ringmay be arbitrarily substituted with halogen atom, C₁-C₄alkyl orC₁-C₄haloalkyl, R¹ is C₁-C₈alkyl, C₁-C₈alkyl arbitrarily substitutedwith R¹⁶, C₃-C₈cycloalkyl, C₃-C₈halocycloalkyl, C₃-C₈alkenyl,C₃-C₈haloalkenyl, phenyl C₃-C₆alkenyl, phenyl C₃-C₆alkenyl substitutedwith (Z)_(p1), C₃-C₈alkynyl, C₃-C₈haloalkynyl, phenyl C₃-C₆alkynyl,phenyl C₃-C₆alkynyl substituted with (Z)_(p1), C₁-C₆alkoxy, —N(R²⁰)R¹⁹,—N═CHR^(19b),—N═C(R^(19b))R^(19a), —C(O)N(R¹⁰)R⁹, —C(S)N(R¹⁰)R⁹, —C(═NR¹¹)OR⁹,—C(═NR¹¹)SR⁹, —C(═NR¹¹)N(R¹⁰)R⁹, phenyl, phenyl substituted with(Z)_(p1), D-1 to D-4, D-6 to D-18, D-21 to D-24, D-26 to D-40, D-42,D-45 to D-58, E-4 to E-9, E-23 to E-28, E-30, E-31, E-34 or E-45,R² is hydrogen atom, C₁-C₆alkyl, C₁-C₆haloalkyl, C₃-C₆cycloalkylC₁-C₄alkyl, C₁-C₄alkoxy C₁-C₄alkyl, C₁-C₄haloalkoxy C₁-C₄alkyl,benzyloxy C₁-C₄alkyl, C₁-C₄alkylthio C₁-C₄alkyl, C₁-C₄haloalkylthioC₁-C₄alkyl, C₁-C₄alkylsulfonyl C₁-C₄alkyl, C₁-C₄haloalkylsulfonylC₁-C₄alkyl, phenylthio C₁-C₄alkyl, phenylthio C₁-C₄alkyl substitutedwith (Z)_(p1), cyano C₁-C₆alkyl, nitro C₁-C₆alkyl, C₁-C₄alkylcarbonylC₁-C₄alkyl, C₁-C₄alkoxycarbonyl C₁-C₄alkyl, C₃-C₆cycloalkyl,C₃-C₆alkenyl, C₃-C₆haloalkenyl, C₃-C₆alkynyl, —SR⁹, —S(O)₂R⁹,—SN(R¹⁸)R¹⁷, —OH, —OR¹⁹, —NHR²⁰,—N(R²⁰)R¹⁹, —N═CHR^(19b), —N═C(R^(19b))R^(19a), —C(O)R⁹, —C(O)OR⁹,—C(O)SR⁹, —C(S)OR⁹ or —C(S)SR⁹,or R¹ and R² together form ═C(R^(2a))R^(1a), and further R¹ and R²together may form 3- to 7-membered ring together with the nitrogen atombonding them by forming C₂ to C₆ alkylene chain, in this case, thealkylene chain may contain one oxygen atom, sulfur atom or nitrogenatom, and may be arbitrarily substituted with C₁-C₆alkyl, formyl,C₁-C₆alkylcarbonyl or C₁-C₆alkoxycarbonyl,R^(1a) and R^(2a) together may form 5- or 6-membered ring together withthe carbon atom bonding them by forming C₄ or C₅ alkylene chain or C₄ orC₅ alkenylene chain, in this case, the alkylene chain and the alkenylenechain may contain one to three oxygen atoms, sulfur atoms or nitrogenatoms, and may be arbitrarily substituted with halogen atom orC₁-C₆alkyl,R³ is cyano, C₁-C₆alkyl, C₁-C₆alkyl arbitrarily substituted with R⁴,C₃-C₈cycloalkyl, C₃-C₈halocycloalkyl, C₃-C₆alkenyl, C₃-C₆haloalkenyl,C₃-C₆alkynyl, C₃-C₆haloalkynyl, —OR⁵, —S(O)_(r)R⁵, —N(R¹⁰)R⁹, —C(O)OR⁹,—C(O)SR⁹, —C(O)NHR¹⁰, —C(O)N(R¹⁰)R⁹, —C(S)OR⁹, —C(S)SR⁹, —C(S)NHR¹⁰,—C(S)N(R¹⁰)R⁹, —CH═NOR¹¹, —C(R⁹)═NOR¹¹, —Si(R¹³)(R¹⁴)R¹², phenyl, phenylsubstituted with (Z)_(p1), D-1 to D-4, D8- to

D-13, D-15 to D-23, D-25 to D-37, D-39, D-40, D-42, D-45 to D-60 or E-4to E-7, E-23 to E27 or E-28,

R⁴ is halogen atom, cyano, C₃-C₆cycloalkyl, C₃-C₆halocycloalkyl, —OH,—OR⁵, —S(O)_(r)R⁵,—N(R¹⁰)R⁹, —N(R¹⁰)C(O)R⁹, —N(R¹⁰)C(O)OR⁹, —N(R¹⁰)C(O)SR⁹,—N(R¹⁰)C(S)OR⁹, —N(R¹⁰)C(S)SR⁹, —N(R¹⁰)S(O)₂R⁹, —Si(R¹³)(R¹⁴)R¹²,phenyl, phenyl substituted with (Z)_(p1), D-1 to D-5, D-8 to D-38, D-41,D-43, D-44, D-47 to D-52 or D-53,R⁵ is C₁-C₆alkyl, C₁-C₆haloalkyl, C₁-C₃haloalkoxy C₁-C₃haloalkyl,C₃-C₈cycloalkyl, C₃-C₈halocycloalkyl, C₂-C₆alkenyl, C₂-C₆haloalkenyl,C₃-C₆alkynyl, C₃-C₆haloalkynyl, phenyl, phenyl substituted with(Z)_(p1), D-1 to D-4, D-7, D-9, D-15 to D-23, D-30 to D-35, D-47 to

D-53, E-3 to E-9, E-23 to E-27 or E-28,

R⁶ is C₁-C₆alkyl, C₁-C₆haloalkyl, C₃-C₆cycloalkyl C₁-C₄alkyl,C₁-C₄alkoxy C₁-C₄alkyl, C₁-C₄alkylthio C₁-C₄alkyl, —S(O)₂R⁹, —CHO,—C(O)R⁹, —C(O)OR⁹, —C(O)SR⁹, —C(S)OR⁹ or

—C(S)SR⁹,

R⁷ is hydrogen atom, C₁-C₆alkyl, C₁-C₆haloalkyl, C₃-C₆alkenyl orC₃-C₆alkynyl,R⁸ is C₁-C₆alkyl,R⁹ is C₁-C₆alkyl, C₁-C₆haloalkyl, C₃-C₆cycloalkyl C₁-C₄alkyl,C₁-C₆alkoxy C₁-C₄alkyl, C₁-C₆alkylthio C₁-C₄alkyl, cyano C₁-C₆alkyl,phenyl C₁-C₄alkyl, phenyl C₁-C₄alkyl substituted with (Z)_(p1),C₃-C₈cycloalkyl, C₃-C₈halocycloalkyl, C₃-C₆alkenyl, C₃-C₆haloalkenyl,C₃-C₆alkynyl, C₃-C₆haloalkynyl, phenyl, phenyl substituted with(Z)_(p1), D-1 to D-4, D-6 to D-35, D-38, D-47 to D-54 or D-55,R¹⁰ is hydrogen atom or C₁-C₆alkyl, or R¹⁰ together with R⁹ may form 5-to 7-membered ring with the nitrogen atom bonding them by formingC₄-C₆alkylene chain, in this case, the alkylene chain may contain oneoxygen atom or sulfur atom, R¹¹ is C₁-C₆alkyl, C₁-C₆haloalkyl, phenylC₁-C₄alkyl, phenyl C₁-C₄alkyl substituted with (Z)_(p1), phenyl orphenyl substituted with (Z)_(p1), or R¹¹ together with R⁹ may form 5- or6-membered ring with the atom bonding them by forming C₂-C₃alkylenechain, in this case, the alkylene chain may be arbitrarily substitutedwith C₁-C₆alkyl,R¹² is C₁-C₆alkyl, phenyl or phenyl substituted with (Z)_(p1),R¹³ and R¹⁴ independently of each other are C₁-C₆alkyl,R¹⁵ is C₁-C₆alkyl, C₁-C₆haloalkyl, phenyl C₁-C₄alkyl, phenyl C₁-C₄alkylsubstituted with (Z)_(p1), phenyl or phenyl substituted with (Z)_(p1),R¹⁶ is halogen atom, cyano, C₃-C₆cycloalkyl, C₃-C₆halocycloalkyl, —OR²⁵,—N(R²⁶)R²⁵, —SH, —S(O)_(r)R²⁷, —SO₂NHR²⁹, —SO₂N(R²⁹)R²⁸, —CHO, —C(O)R²⁸,—C(O)OR²⁸, —C(O)NHR²⁹,—C(O)N(R²⁹)R²⁸, —C(O)N(R²⁹)OR²⁸, —C(S)NHR²⁹, —C(S)N(R²⁹)R²⁸,—C(R³¹)═NOH, —C(R³¹)═NOR³⁰, —C(═NR³¹)OR³⁰, —C(═NR³¹)SR³⁰,—C(═NR³¹)N(R²⁹)R³⁰, —C(═NOR³¹)NHR²⁹, —C(═NOR³¹)N(R²⁹)R³⁰,—Si(R¹³)(R¹⁴)R¹², phenyl, phenyl substituted with (Z)_(p1), D-1 to D-60,E-1 to E-49 or M-1 to M-22,R¹⁷ is C₁-C₆alkyl, C₁-C₄alkoxy C₁-C₄alkyl, C₁-C₆alkoxycarbonylC₁-C₄alkyl, phenyl C₁-C₄alkyl, phenyl C₁-C₄alkyl substituted with(Z)_(p1) or C₁-C₆alkoxycarbonyl,R¹⁸ is C₁-C₆alkyl, phenyl C₁-C₄alkyl or phenyl C₁-C₄alkyl substitutedwith (Z)_(p1), or R¹⁸ together with R¹⁷ may form 5- or 6-membered ringwith the nitrogen atom bonding them by forming C₄-C₅alkylene chain, inthis case, the alkylene chain may contain one oxygen atom or sulfuratom, and may be arbitrarily substituted with methyl or methoxy,R¹⁹ is C₁-C₆alkyl, C₁-C₆alkyl arbitrarily substituted with R¹⁶,C₃-C₆cycloalkyl, C₃-C₆halocycloalkyl, C₃-C₆alkenyl, C₃-C₆haloalkenyl,C₃-C₆alkynyl, —CHO, —C(O)R²⁸, —C(O)OR²⁸, —C(O)NHR²⁹, —C(O)N(R²⁹)R²⁸,—C(S)NHR²⁹, —C(S)N(R²⁹)R²⁸, —S(O)₂R²⁸, —S(O)₂NHR²⁹, —S(O)₂N(R²⁹)R²⁸,phenyl, phenyl substituted with (Z)_(p1), D-1 to D-13, D-15 to D-25,D-30 to D-37, D-39, D-40, D-42, D-45 to D-60, E-5, E-7, E-9, E-24, E-25,E-27, E-28, E-30 or E-31,R^(19a) is C₁-C₆alkyl, C₁-C₆haloalkyl, C₃-C₆cycloalkyl, phenyl, phenylsubstituted with (Z)_(p1), D-1 to D-4, D-8 to D-10, D-15 to D-23, D-47to D-55, E-4 to E-7, E-23 to E-27 or E-28,R^(19b) is hydrogen atom or C₁-C₆alkyl, or R^(19a) together with R^(19b)may form 5- or 6-membered ring with the carbon atom bonding them byforming C₄-C₅alkylene chain, in this case, the alkylene chain maycontain one oxygen atom or sulfur atom,R²⁰ is hydrogen atom, C₁-C₆alkyl, C₁-C₆haloalkyl, C₁-C₄alkoxyC₁-C₄alkyl, C₁-C₄alkylthio C₁-C₄alkyl, cyano C₁-C₆alkyl,C₁-C₄alkoxycarbonyl C₁-C₄alkyl, C₂-C₆alkenyl, C₃-C₆alkynyl, —CHO,—C(O)R⁹, —C(O)OR⁹, —C(O)SR⁹, —C(S)OR⁹, —C(S)SR⁹ or C₁-C₆alkylsulfonyl,R²² is halogen atom, cyano, C₁-C₆alkyl, C₁-C₆haloalkyl, C₁-C₆alkoxy,C₁-C₆alkoxycarbonyl,—C(O)NH₂ or —C(S)NH₂, when q1, q2, q3 or q4 is an integer of 2 or more,each R²² may be identical with or different from each other, further incase where two R²²s are present on the same carbon atom, the two R²²stogether may form oxo, thioxo, imino, C₁-C₆alkylimino, C₁-C₆alkoxyiminoor C₁-C₆alkylidene,R²³ is hydrogen atom, C₁-C₆alkyl, C₁-C₆alkyl arbitrarily substitutedwith R³², C₃-C₆cycloalkyl, C₃-C₆alkenyl, C₃-C₆alkynyl, —OH, benzyloxy,—CHO, —C(O)R³³, —C(O)OR³³, —C(O)SR³³, —C(O)NHR³⁴, —C(O)N(R³⁴)R³³,—S(O)₂R³³, phenyl, phenyl substituted with (Z)_(p1) or D-5,R²⁵ is hydrogen atom, C₁-C₆alkyl, C₁-C₆haloalkyl, C₁-C₄alkoxyC₁-C₄alkyl, C₁-C₄alkylthio C₁-C₄alkyl, cyano C₁-C₆alkyl, phenylC₁-C₄alkyl, phenyl C₁-C₄alkyl substituted with (Z)_(p1), C₃-C₆alkenyl,C₃-C₆alkynyl, —CHO, —C(O)R³³, —C(O)OR³³, —C(O)SR³³, —C(O)NHR³⁴,—C(O)N(R³⁴)R³³, —C(S)R³³, —C(S)OR³³, —C(S)SR³³, —C(S)NHR³⁴,—C(S)N(R³⁴)R³³, —S(O)₂R³³, —S(O)₂N(R³⁴)R³³, di(C₁-C₆alkyl)phosphoryl,di(C₁-C₆alkyl)thiophosphoryl, tri(C₁-C₄alkyl)silyl, phenyl or phenylsubstituted with (Z)_(p1),R²⁶ is hydrogen atom, C₁-C₆alkyl, C₃-C₆alkenyl, C₃-C₆alkynyl orC₁-C₆alkoxy, or R²⁶ together with R²⁵ may form 4- to 6-membered ringwith the nitrogen atom bonding them by forming C₃-C₅alkylene chain, inthis case, the alkylene chain may contain one oxygen atom, sulfur atomor nitrogen atom, and may substituted with C₁-C₆alkyl, oxo or thioxo,R²⁷ is C₁-C₆alkyl, C₁-C₆haloalkyl, hydroxy C₁-C₆alkyl, C₁-C₄alkoxyC₁-C₄alkyl, C₁-C₄alkylthio C₁-C₄alkyl, C₁-C₄alkylcarbonyl C₁-C₄alkyl,C₁-C₄alkoxycarbonyl C₁-C₄alkyl, di(C₁-C₄alkyl)aminocarbonyl C₁-C₄alkyl,tri(C₁-C₄alkyl)silyl C₁-C₄alkyl, phenyl C₁-C₄alkyl, phenyl C₁-C₄alkylsubstituted with (Z)_(p1), C₃-C₆alkenyl, C₃-C₆alkynyl,C₁-C₆alkylcarbonyl, C₁-C₆alkylthio, phenylthio, phenylthio substitutedwith (Z)_(p1),—C(O)NHR³⁴, —C(O)N(R³⁴)R³³, —C(S)NHR³⁴, —C(S)N(R³⁴)R³³, phenyl, phenylsubstituted with (Z)_(p1), D-21, D-35, D-47 or D-50,R²⁸ is C₁-C₆alkyl, C₁-C₆alkyl arbitrarily substituted with R³²,C₃-C₆cycloalkyl, C₃-C₆halocycloalkyl, C₃-C₆alkenyl, C₃-C₆haloalkenyl,C₃-C₆alkynyl, C₃-C₆haloalkynyl, phenyl, phenyl substituted with(Z)_(p1), D-1 to D-60 or E-1 to E-49,R²⁹ is hydrogen atom, C₁-C₆alkyl, C₁-C₄alkoxy C₁-C₄alkyl, C₁-C₄alkylthioC₁-C₄alkyl, cyano C₁-C₆alkyl, C₃-C₆alkenyl or C₃-C₆alkynyl, or R²⁹together with R²⁸ may form 3- to 6-membered ring with the nitrogen atombonding them by forming C₂-C₅alkylene chain, in this case, the alkylenechain may contain one oxygen atom or sulfur atom, R³⁰ is C₁-C₆alkyl,C₁-C₄alkoxy C₁-C₄alkyl, C₁-C₄alkylthio C₁-C₄alkyl, C₃-C₆cycloalkylC₁-C₄alkyl, tri(C₁-C₆alkyl)silyl C₁-C₄alkyl, phenyl C₁-C₄alkyl, phenylC₁-C₄alkyl substituted with (Z)_(p1), C₃-C₈alkenyl, C₃-C₈haloalkenyl,C₃-C₈alkynyl or C₃-C₈haloalkynyl,R³¹ is hydrogen atom, C₁-C₆alkyl, C₁-C₆haloalkyl or C₃-C₆cycloalkyl, orR³¹ together with R³⁰ may form 5- or 6-membered ring with the atombonding them by forming C₂-C₃alkylene chain, in this case, the alkylenechain may be arbitrarily substituted with C₁-C₆alkyl,R³² is halogen atom, cyano, C₃-C₈cycloalkyl, C₃-C₈halocycloalkyl, —OR³³,—OC(O)R³³,—OC(O)NHR³³, —OC(O)N(R³⁴)R³³, —S(O)_(r)R³³, —SC(O)R³³, —SC(O)NHR³³,—SC(O)N(R³⁴)R³³, —N(R³⁴)CHO, —N(R³⁴)C(O)R³³, —N(R³⁴)C(O)OR³³, —C(O)OR³³,—C(O)NHR³⁴, —C(O)N(R³⁴)R³³, phenyl, phenyl substituted with (Z)_(p1),D-1 to D-60 or E-1 to E-49,R³³ is C₁-C₆alkyl, C₁-C₆haloalkyl, C₃-C₆cycloalkyl C₁-C₄alkyl,C₁-C₄alkoxy C₁-C₄alkyl, C₁-C₄haloalkoxy C₁-C₄alkyl, C₁-C₄alkylthioC₁-C₄alkyl, C₁-C₄haloalkylthio C₁-C₄alkyl, C₁-C₄alkylsulfonylC₁-C₄alkyl, C₁-C₄haloalkylsulfonyl C₁-C₄alkyl, cyano C₁-C₆alkyl, phenylC₁-C₄alkyl, phenyl C₁-C₄alkyl substituted with (Z)_(p1),C₃-C₆cycloalkyl, C₃-C₆halocycloalkyl, C₃-C₆alkenyl, C₃-C₆haloalkenyl,C₃-C₆alkynyl, phenyl, phenyl substituted with (Z)_(p1), D-1 to D-4, D-8to D-13, D-15 to D-18, D-21, D-29 to D-37, D-47 to D-55, E-5, E-7, E-9,E-24, E-25,

E-27, E-28, E-30, E-31 or E-34,

R³⁴ is hydrogen atom, C₁-C₆alkyl, C₁-C₆haloalkyl, C₃-C₆alkenyl orC₃-C₆alkynyl, or R³⁴ together with R³³ may form 3- to 6-membered ringwith the nitrogen atom bonding them by forming C₂-C₅alkylene chain, inthis case, the alkylene chain may contain one oxygen atom or sulfuratom.(3) The isoxazoline-substituted benzamide compound or the salt thereofas set forth in (2), wherein

G is G-1, G-3, G-4, G-13, G-14, G-17, G-18, G-20, G-21 or G-22,

X is halogen atom, cyano, nitro, —SF₅, C₁-C₆alkyl, C₁-C₆alkylarbitrarily substituted with R⁴, C₃-C₈cycloalkyl, C₃-C₈halocycloalkyl,C₂-C₆alkenyl, C₂-C₆haloalkenyl, C₂-C₆alkynyl, C₂-C₆haloalkynyl, —OR⁵,—OSO₂R⁵, —S(O)_(r)R⁵, —C(O)OR⁹, —C(O)SR⁹, —C(S)OR⁹, —C(S)SR⁹,—C(S)NHR¹⁰, —C(S)N(R¹⁰)R⁹, —CH═NOR¹¹, —C(R⁹)═NOR¹¹, —Si(R¹³)(R¹⁴)R¹²,E-10, E-12, E-18, E-32, E-35 or E-43, when m is 2 or 3, each X may beidentical with or different from each other,further, when two Xs are adjacent, the adjacent two Xs may form5-membered or 6-membered ring together with carbon atoms to which thetwo Xs are bonded by forming —CF₂OCF₂—, —OCF₂O—, —CF₂OCF₂O— or—OCF₂CF₂O—,Y is halogen atom, cyano, nitro, C₁-C₆alkyl, C₁-C₆alkyl arbitrarilysubstituted with R⁴, —OR⁵, —OSO₂R⁵, —S(O)_(r)R⁵, —NHR⁷, —N(R⁷)R⁶,—N═C(R⁹)OR⁸, —C(O)NH₂ or —C(S)NH₂, when n is 2 or 3, each Y may beidentical with or different from each other,R¹ is C₁-C₈alkyl, C₁-C₆alkyl arbitrarily substituted with R¹⁶,C₃-C₈cycloalkyl, C₃-C₈halocycloalkyl, C₃-C₈alkenyl, C₃-C₈haloalkenyl,C₃-C₈alkynyl, C₃-C₈haloalkynyl,—N(R²⁰)R¹⁹, —C(O)N(R¹⁰)R⁹, —C(S)N(R¹⁰)R⁹, phenyl substituted with(Z)_(p1), D-8 to D-18, D-21 to D-24, D-26 to D-40, D-42, D-45 to D-58,E-4, E-5, E-7, E-8, E-9, E-23 to E-25, E-27, E-28, E-30, E-31 or E-34,R² is hydrogen atom, C₁-C₆alkyl, C₁-C₆haloalkyl, C₁-C₄alkoxy C₁-C₄alkyl,C₁-C₄alkylthio C₁-C₄alkyl, cyano C₁-C₆alkyl, C₃-C₆cycloalkyl,C₃-C₆alkenyl, C₃-C₆alkynyl, —OH, C₁-C₆alkoxy, C₁-C₆alkylcarbonyloxy,C₁-C₆alkoxycarbonyloxy, C₁-C₆alkylsulfonyloxy, C₁-C₆haloalkylthio,phenylthio, phenylthio substituted with (Z)_(p1), C₁-C₆alkylsulfonyl,—SN(R¹⁸)R¹⁷, —NHR²⁰, —N═CHR^(19b), —N═C(R^(19b))R^(19a), —C(O)R⁹,—C(O)OR⁹, —C(O)SR⁹, —C(S)OR⁹ or —C(S)SR⁹, or R² together with R¹ mayform 3- to 7-membered ring with the nitrogen atom bonding them byforming C₂-C₆alkylene chain, in this case, the alkylene chain maycontain one oxygen atom or sulfur atom, R³ is C₁-C₆alkyl,C₁-C₆haloalkyl, C₃-C₆cycloalkyl C₁-C₄alkyl, C₃-C₆halocycloalkylC₁-C₄alkyl, C₁-C₄alkoxy C₁-C₄alkyl, C₁-C₄haloalkoxy C₁-C₄alkyl,C₁-C₄alkylthio C₁-C₄alkyl, C₁-C₄alkylsulfinyl C₁-C₄alkyl,C₁-C₄alkylsulfonyl C₁-C₄alkyl,C₁-C₄haloalkylthio C₁-C₄alkyl, C₁-C₄haloalkylsulfinyl C₁-C₄alkyl,C₁-C₄haloalkylsulfonyl C₁-C₄alkyl, cyano C₁-C₆alkyl, C₁-C₄alkoxyC₁-C₄haloalkyl, C₁-C₄haloalkoxy C₁-C₄haloalkyl, C₁-C₄alkylthioC₁-C₄haloalkyl, C₁-C₄alkylsulfinyl C₁-C₄haloalkyl, C₁-C₄alkylsulfonylC₁-C₄haloalkyl, C₁-C₄haloalkylthio C₁-C₄haloalkyl,C₁-C₄haloalkylsulfinyl C₁-C₄haloalkyl, C₁-C₄haloalkylsulfonylC₁-C₄haloalkyl, cyano C₁-C₆haloalkyl, C₃-C₈cycloalkyl,C₃-C₈halocycloalkyl, E-4 to E-7, E-23 to E-27 or E-28,R⁴ is halogen atom, cyano, —OH, C₁-C₆alkoxy, C₁-C₆haloalkoxy,C₁-C₆alkylthio, C₁-C₆haloalkylthio, C₁-C₆alkylsulfinyl,C₁-C₆haloalkylsulfinyl, C₁-C₆alkylsulfonyl, C₁-C₆haloalkylsulfonyl ortri(C₁-C₆alkyl)silyl,R⁵ is C₁-C₆alkyl, C₁-C₆haloalkyl, C₁-C₃haloalkoxy C₁-C₃haloalkyl,C₃-C₈cycloalkyl, C₃-C₈halocycloalkyl, C₂-C₆alkenyl, C₂-C₆haloalkenyl,C₃-C₆alkynyl,C₃-C₆haloalkynyl, E-4 to E-9, E-23 to E-27 or E-28,R⁶ is C₁-C₆alkyl, C₁-C₆haloalkyl, —S(O)₂R⁹, —CHO, —C(O)R⁹, —C(O)OR⁹,—C(O)SR⁹, —C(S)OR⁹ or —C(S)SR⁹,R⁷ is hydrogen atom, C₁-C₆alkyl or C₁-C₆haloalkyl,R⁹ is C₁-C₆alkyl, C₁-C₆haloalkyl, C₃-C₆cycloalkyl C₁-C₄alkyl,C₁-C₆alkoxy C₁-C₄alkyl, C₁-C₆alkylthio C₁-C₄alkyl, cyano C₁-C₆alkyl,phenyl C₁-C₄alkyl, C₃-C₈cycloalkyl, C₃-C₈halocycloalkyl, C₃-C₆alkenyl orC₃-C₆alkynyl,R¹⁰ is hydrogen atom or C₁-C₆alkyl, or R¹⁰ together with R⁹ may form 5-or 6-membered ring with the nitrogen atom bonding them by forming C₄ orC₅alkylene chain, in this case, the alkylene chain may contain oneoxygen atom or sulfur atom,R¹¹ is C₁-C₆alkyl or C₁-C₆haloalkyl, or R¹¹ together with R⁹ may form 5-or 6-membered ring with the atom bonding them by forming C₂ orC₃alkylene chain, in this case, the alkylene chain may be arbitrarilysubstituted with C₁-C₆alkyl,R¹⁵ is C₁-C₆alkyl or C₁-C₆haloalkyl,R¹⁶ is halogen atom, cyano, C₃-C₆cycloalkyl, C₃-C₆halocycloalkyl, —OR²⁵,—N(R²⁶)R²⁵, —S(O)_(r)R²⁷, —SO₂NHR²⁹, —SO₂N(R²⁹)R²⁸, —CHO, —C(O)R²⁸,—C(O)OR²⁸, —C(O)NHR²⁹, —C(O)N(R²⁹)R²⁸, —C(O)N(R²⁹)OR²⁸, —C(S)NHR²⁹,—C(S)N(R²⁹)R²⁸, —C(R³¹)═NOH, —C(R³¹)═NOR³⁰, —C(═NR³¹)OR³⁰,—C(═NR³¹)SR³⁰, —C(═NR³¹)N(R²⁹)R³⁰, —C(═NOR³¹)NHR²⁹, —C(═NOR³¹)N(R²⁹)R³⁰,phenyl, phenyl substituted with (Z)_(p1), D-1 to D-4, D-8 to D-42, D-47to D-55, E-4 to E-12, E-14, E-16 to E-19, E-21 to E-23, E-26 to E-35,E-40 to E-45, E-48, M-2, M-3, M-5, M-8 to M-10, M-14, M-15 or M-16,R¹⁷ is C₁-C₆alkyl, C₁-C₆alkoxycarbonyl C₁-C₄alkyl orC₁-C₆alkoxycarbonyl,R¹⁸ is C₁-C₆alkyl or benzyl,R¹⁹ is C₁-C₆alkyl, C₁-C₆haloalkyl, C₃-C₆cyclaolakyl C₁-C₆alkyl, phenylC₁-C₆alkyl, phenyl C₁-C₆alkyl substituted with (Z)_(p1),C₃-C₆cycloalkyl, C₃-C₆alkenyl, C₃-C₆haloalkenyl, C₃-C₆alkynyl, —C(O)R²⁸,—C(O)OR²⁸, —C(O)NHR²⁹, —C(O)N(R²⁹)R²⁸, —C(S)NHR²⁹, —C(S)N(R²⁹)R²⁸,C₁-C₆alkylsulfonyl, C₁-C₆haloalkylsulfonyl, phenylsulfonyl,phenylsulfonyl substituted with (Z)_(p1), phenyl, phenyl substitutedwith (Z)_(p1), D-1 to D-4, D-18, D-21, D-25, D-30 to D-35, D-47 to D-55or D-56, R^(19a) is C₁-C₆alkyl,R^(19b) is hydrogen atom or C₁-C₆alkyl,R²⁰ is hydrogen atom, C₁-C₆alkyl, C₁-C₄alkoxy C₁-C₄alkyl, C₁-C₄alkylthioC₁-C₄alkyl, cyano C₁-C₆alkyl, C₃-C₆alkenyl, C₃-C₆alkynyl, —CHO,C₁-C₆alkylcarbonyl, C₁-C₆haloalkylcarbonyl, C₁-C₆alkoxycarbonyl,C₁-C₆haloalkoxycarbonyl or C₁-C₆alkylsulfonyl,R²² is C₁-C₄alkyl or C₁-C₄haloalkyl, or two R²²s present on the samecarbon atom may together form oxo, or thioxo,R²³ is hydrogen atom, C₁-C₆alkyl, —CHO, C₁-C₆alkylcarbonyl,C₁-C₆haloalkylcarbonyl, C₁-C₆alkoxycarbonyl, C₁-C₆alkylsulfonyl orC₁-C₆haloalkylsulfonyl,R²⁵ is hydrogen atom, C₁-C₆alkyl, C₁-C₆haloalkyl, —C(O)R³³, —C(O)OR³³,—C(O)SR³³, —C(O)NHR³⁴, —C(O)N(R³⁴)R³³, —C(S)R³³, —C(S)OR³³, —C(S)SR³³,—C(S)NHR³⁴, —C(S)N(R³⁴)R³³, —S(O)₂R³³, —S(O)₂N(R³⁴)R³³,di(C₁-C₆alkyl)thiophosphoryl, phenyl or phenyl substituted with(Z)_(p1),R²⁶ is hydrogen atom or C₁-C₆alkyl, or R²⁶ together with R²⁵ may form 4-to 6-membered ring with the nitrogen atom bonding them by formingC₃-C₅alkylene chain, in this case, the alkylene chain may contain oneoxygen atom, sulfur atom or nitrogen atom, and may be substituted withC₁-C₆alkyl, oxo or thioxo,R²⁷ is C₁-C₆alkyl, C₁-C₆haloalkyl, tri(C₁-C₄alkyl)silyl C₁-C₄alkyl,C₁-C₆alkylthio, —C(O)NHR³⁴, —C(O)N(R³⁴)R³³, —C(S)NHR³⁴, —C(S)N(R³⁴)R³³,phenyl, phenyl substituted with (Z)_(p1), D-47 or D-50,R²⁸ is C₁-C₆alkyl, C₁-C₆alkyl arbitrarily substituted with R³²,C₃-C₆cycloalkyl, C₃-C₆halocycloalkyl, C₃-C₆alkenyl, C₃-C₆haloalkenyl,C₃-C₆alkynyl, C₃-C₆haloalkynyl, phenyl or phenyl substituted with(Z)_(p1),R²⁹ is hydrogen atom, C₁-C₆alkyl, C₃-C₆alkenyl or C₃-C₆alkynyl, or R²⁹together with R²⁸ may form 3- to 6-membered ring with the nitrogen atombonding them by forming C₂-C₅alkylene chain, in this case, the alkylenechain may contain one oxygen atom or sulfur atom,R³⁰ is C₁-C₆alkyl, C₃-C₆cycloalkyl C₁-C₄alkyl, phenyl C₁-C₄alkyl, phenylC₁-C₄alkyl substituted with (Z)_(p1), C₃-C₈alkenyl or C₃-C₈alkynyl,R³¹ is hydrogen atom or C₁-C₆alkyl, or R³¹ together with R³⁰ may form 5-or 6-membered ring with the atom bonding them by forming C₂ orC₃alkylene chain, in this case, the alkylene chain may be arbitrarilysubstituted with C₁-C₆alkyl,R³² is halogen atom, cyano, C₃-C₆cycloalkyl, C₃-C₆halocycloalkyl,C₁-C₄alkoxy, C₁-C₄haloalkoxy, C₁-C₄alkylthio, C₁-C₄haloalkylthio,C₁-C₄alkoxycarbonyl, —C(O)NH₂, C₁-C₄alkylaminocarbonyl,di(C₁-C₄alkyl)aminocarbonyl, phenyl or phenyl substituted with (Z)_(p1),R³³ is C₁-C₆alkyl, C₁-C₆haloalkyl, C₁-C₄alkoxy C₁-C₄alkyl,C₁-C₄alkylthio C₁-C₄alkyl, C₁-C₄alkylsulfonyl C₁-C₄alkyl, phenylC₁-C₄alkyl, phenyl C₁-C₄alkyl substituted with (Z)_(p1),C₃-C₆cycloalkyl, C₃-C₆halocycloalkyl, C₃-C₆alkenyl, C₃-C₆alkynyl, phenylor phenyl substituted with (Z)_(p1),R³⁴ is hydrogen atom or C₁-C₆alkyl,m is an integer of 1 to 3,n is an integer of 0 to 2,q1 is 0,q2 is an integer of 0 to 3,q3 is an integer of 0 to 2, andq4 is an integer of 0 to 2.(4) The isoxazoline-substituted benzamide compound or the salt thereofas set forth in (3), whereinA¹ is carbon atom or nitrogen atom,A² and A³ are carbon atom,

G is G-1,

X is halogen atom, cyano, nitro, —SF₅, C₁-C₆alkyl, C₁-C₆alkylarbitrarily substituted with R⁴, C₃-C₈cycloalkyl, C₃-C₈halocycloalkyl,C₂-C₆alkenyl, C₂-C₆haloalkenyl, C₂-C₆alkynyl, C₂-C₆haloalkynyl, —OR⁵,—OSO₂R⁵, —S(O)_(r)R⁵ or tri(C₁-C₆alkyl)silyl, when m is 2 or 3, each Xmay be identical with or different from each other, further, when two Xsare adjacent, the adjacent two Xs may form 5-membered or 6-membered ringtogether with carbon atoms to which the two Xs are bonded by forming

—CF₂OCF₂—, —OCF₂O—, —CF₂OCF₂O— or —OCF₂CF₂O—,

Y is halogen atom, cyano, nitro, C₁-C₆alkyl, C₁-C₆alkyl arbitrarilysubstituted with R⁴, —OR⁵, —OSO₂R⁵, —S(O)_(r)R⁵, —NHR⁷, —N(R⁷)R⁶,—C(O)NH₂ or —C(S)NH₂, when n is 2 or 3, each Y may be identical with ordifferent from each other,R¹ is C₁-C₆alkyl, C₁-C₆alkyl arbitrarily substituted with R¹⁶,C₃-C₆cycloalkyl, C₃-C₆halocycloalkyl, C₃-C₆alkenyl, C₃-C₆haloalkenyl,C₃-C₆alkynyl, C₃-C₆haloalkynyl, —N(R²⁰)R¹⁹, —C(O)N(R¹⁰)R⁹,—C(S)N(R¹⁰)R⁹, phenyl substituted with (Z)_(p1), D-8, D-10, D-11, D-13to D-15, D-17, D-18, D-21 to D-23, D-26 to D-37, D-39, D-40, D-42, D-45,D-47 to D-54, D-56, D-58, E-4, E-5, E-7 or E-9,R² is hydrogen atom, C₁-C₆alkyl, C₁-C₄alkoxy C₁-C₄alkyl, C₁-C₄alkylthioC₁-C₄alkyl, cyano C₁-C₆alkyl, C₃-C₆cycloalkyl, C₃-C₆alkenyl,C₃-C₆alkynyl, —OH, C₁-C₆alkylcarbonyloxy, C₁-C₆alkylsulfonyloxy, —NH₂,—C(O)R⁹, —C(O)OR⁹, —C(O)SR⁹, —C(S)OR⁹ or —C(S)SR⁹,R³ is C₁-C₆haloalkyl, C₁-C₄alkoxy C₁-C₄haloalkyl, C₁-C₄haloalkoxyC₁-C₄haloalkyl, C₁-C₄alkylthio C₁-C₄haloalkyl, C₁-C₄haloalkylthioC₁-C₄haloalkyl, cyano C₁-C₆haloalkyl or C₃-C₈halocycloalkyl,R⁴ is halogen atom, cyano, —OH, C₁-C₆alkoxy, C₁-C₆haloalkoxy,C₁-C₆alkylthio, C₁-C₆haloalkylthio, C₁-C₆alkylsulfinyl,C₁-C₆haloalkylsulfinyl, C₁-C₆alkylsulfonyl, C₁-C₆haloalkylsulfonyl ortri(C₁-C₆alkyl)silyl,R⁵ is C₁-C₆alkyl, C₁-C₆haloalkyl, C₁-C₃haloalkoxy C₁-C₃haloalkyl,C₃-C₈cycloalkyl, C₃-C₈halocycloalkyl, C₂-C₆alkenyl, C₂-C₆haloalkenyl,C₃-C₆alkynyl or C₃-C₆haloalkynyl,R⁶ is C₁-C₆alkyl, C₁-C₆haloalkyl, —CHO, C₁-C₆alkylcarbonyl,C₁-C₆haloalkylcarbonyl, C₃-C₆cycloalkylcarbonyl,C₃-C₆halocycloalkylcarbonyl, C₁-C₆alkoxycarbonyl,C₁-C₆haloalkoxycarbonyl, C₁-C₆alkylthiocarbonyl,C₁-C₆alkoxythiocarbonyl, C₁-C₆alkyldithiocarbonyl, C₁-C₆alkylsulfonyl orC₁-C₆haloalkylsulfonyl,R⁷ is hydrogen atom or C₁-C₆alkyl,R⁹ is C₁-C₆alkyl, C₁-C₆haloalkyl, C₃-C₆cycloalkyl C₁-C₄alkyl,C₁-C₆alkoxy C₁-C₄alkyl, C₁-C₆alkylthio C₁-C₄alkyl, cyano C₁-C₆alkyl,C₃-C₈cycloalkyl, C₃-C₆alkenyl or C₃-C₆alkynyl,R¹⁶ is halogen atom, cyano, C₃-C₆cycloalkyl, C₃-C₆halocycloalkyl, —OR²⁵,—N(R²⁶)R²⁵, —S(O)_(r)R²⁷, —SO₂NHR²⁹, —SO₂N(R²⁹)R²⁸, —C(O)R²⁸, —C(O)OR²⁸,—C(O)NHR²⁹, —C(O)N(R²⁹)R²⁸, —C(O)N(R²⁹)OR²⁸, —C(S)NHR²⁹, —C(S)N(R²⁹)R²⁸,—C(R³¹)═NOH, —C(R³¹)═NOR³⁰, —C(═NR³¹)OR³⁰, —C(═NR³¹)SR³⁰, phenyl, phenylsubstituted with (Z)_(p1), D-1 to D-4, D-8 to D-38, D-47 to D-55, E-4 toE-12, E-18, E-19, E-32, E-35, E-43, M-2, M-3,

M-5, M-8, M-9 or M-10,

R¹⁹ is C₁-C₆haloalkyl, C₃-C₆cycloalkyl, —C(O)R²⁸, —C(O)OR²⁸, —C(O)NHR²⁹,—C(O)N(R²⁹)R²⁸, —C(S)NHR²⁹, —C(S)N(R²⁹)R²⁸, phenyl, phenyl substitutedwith (Z)_(p1), D-3,

D-4, D-21, D-47, D-50, D-51, D-53 or D-54,

R²⁰ is hydrogen atom, C₁-C₆alkyl, C₁-C₄alkoxy C₁-C₄alkyl, C₁-C₄alkylthioC₁-C₄alkyl, cyano C₁-C₆alkyl, C₃-C₆alkenyl, C₃-C₆alkynyl, —CHO,C₁-C₆alkylcarbonyl, C₁-C₆alkoxycarbonyl or C₁-C₆alkylsulfonyl,R²⁵ is C₁-C₆alkyl, C₁-C₆haloalkyl, C₁-C₆alkylcarbonyl,C₁-C₆alkoxycarbonyl, C₁-C₆alkylaminocarbonyl,di(C₁-C₆alkyl)aminocarbonyl or C₁-C₆alkylsulfonyl,R²⁶ is hydrogen atom or C₁-C₆alkyl,R²⁷ is C₁-C₆alkyl, C₁-C₆haloalkyl or tri(C₁-C₄alkyl)silyl C₁-C₄alkyl,R²⁸ is C₁-C₆alkyl, C₁-C₆haloalkyl, C₃-C₆cycloalkyl C₁-C₄alkyl,C₁-C₄alkoxy C₁-C₄alkyl, C₁-C₄alkylthio C₁-C₄alkyl, cyano C₁-C₆alkyl,phenyl C₁-C₄alkyl, phenyl C₁-C₄alkyl substituted with (Z)_(p1),C₃-C₆cycloalkyl, C₃-C₆alkenyl, C₃-C₆haloalkenyl, C₃-C₆alkynyl, phenyl orphenyl substituted with (Z)_(p1),R²⁹ is hydrogen atom, C₁-C₆alkyl, C₃-C₆alkenyl or C₃-C₆alkynyl,R³⁰ is C₁-C₆alkyl or C₃-C₆cycloalkyl C₁-C₄alkyl,R³¹ is hydrogen atom or C₁-C₆alkyl, or R³¹ together with R³⁰ may form 5-or 6-membered ring with the atom bonding them by forming C₂ orC₃alkylene chain.(5) The isoxazoline-substituted benzamide compound or the salt thereofas set forth in (4), whereinX is halogen atom, cyano, nitro, —SF₅, C₁-C₆alkyl, C₁-C₆haloalkyl,hydroxy C₁-C₆haloalkyl, C₁-C₆alkoxy C₁-C₆haloalkyl, C₁-C₆haloalkoxyC₁-C₆haloalkyl, C₃-C₈halocycloalkyl, —OR⁵, —OSO₂R⁵ or —S(O)_(r)R⁵, whenm is 2 or 3, each X may be identical with or different from each other,Y is halogen atom, cyano, nitro, C₁-C₄alkyl, C₁-C₄haloalkyl,C₁-C₄alkoxy, C₁-C₄haloalkoxy, C₁-C₆alkylthio, C₁-C₆haloalkylthio,C₁-C₆alkylsulfonyl, C₁-C₆haloalkylsulfonyl, —NHR⁷ or —N(R⁷)R⁶,R¹ is C₁-C₆alkyl, C₁-C₆alkyl arbitrarily substituted with R¹⁶,C₃-C₆cycloalkyl, E-4, E-5, C₃-C₆alkenyl, C₃-C₆haloalkenyl, C₃-C₆alkynyl,—N(R²⁰)R¹⁹, D-8, D-10, D-13 to D-15, D-18, D-21, D-34, D-35, D-47, D-48,D-50 to D-53 or D-54,R² is hydrogen atom, C₁-C₆alkyl, C₁-C₄alkoxy C₁-C₄alkyl, cyanoC₁-C₆alkyl, C₃-C₆alkynyl, —C(O)R⁹ or —C(O)OR⁹,R³ is C₁-C₆haloalkyl or C₃-C₈halocycloalkyl,R⁵ is C₁-C₆alkyl, C₁-C₆haloalkyl or C₁-C₃haloalkoxy C₁-C₃haloalkyl,R⁶ is C₁-C₆alkyl, —CHO, C₁-C₆alkylcarbonyl, C₁-C₆haloalkylcarbonyl,C₁-C₆alkoxycarbonyl, C₁-C₆alkylthiocarbonyl, C₁-C₆alkoxythiocarbonyl,C₁-C₆alkyldithiocarbonyl, C₁-C₆alkylsulfonyl or C₁-C₆haloalkylsulfonyl,R⁹ is C₁-C₆alkyl, C₁-C₆alkoxy C₁-C₄alkyl, C₁-C₆alkylthio C₁-C₄alkyl,C₃-C₈cycloalkyl, C₃-C₆alkenyl or C₃-C₆alkynyl,R¹⁶ is halogen atom, cyano, C₃-C₆cycloalkyl, C₃-C₆halocycloalkyl,C₁-C₆alkoxy, C₁-C₆haloalkoxy, C₁-C₆alkylthio, C₁-C₆haloalkylthio,C₁-C₆alkylsulfinyl, C₁-C₆haloalkylsulfinyl, C₁-C₆alkylsulfonyl,C₁-C₆haloalkylsulfonyl, C₁-C₆alkylcarbonyl,—C(O)OR²⁸, —C(O)NHR²⁹, —C(O)N(R²⁹)R²⁸, —C(S)NH₂, —C(R³¹)═NOH,—C(R³¹)═NOR³⁰, phenyl, phenyl substituted with (Z)_(p1), D-1 to D-4, D-8to D-38, D-47 to D-55, E-4 to E-7, E-10, E-11 or E-32,R¹⁹ is C₁-C₆haloalkyl, —C(O)R²⁸, —C(O)OR²⁸, phenyl, phenyl substitutedwith (Z)_(p1), D-3, D-4, D-21, D-47, D-50, D-51, D-53 or D-54,R²⁰ is hydrogen atom or C₁-C₆alkyl,R²⁸ is C₁-C₆alkyl, C₁-C₆haloalkyl, C₃-C₆cycloalkyl C₁-C₄alkyl,C₃-C₆cycloalkyl, C₃-C₆alkenyl or C₃-C₆alkynyl,R²⁹ is hydrogen atom or C₁-C₆alkyl,R³⁰ is C₁-C₆alkyl,R³¹ is hydrogen atom or C₁-C₆alkyl, andn is an integer of 0 or 1.(6) 3,5-Bis (substituted aryl) substituted isoxazoline compound offormula (2) or a salt thereof:

whereinA¹ is carbon atom or nitrogen atom,X¹ is halogen atom, —SF₅, C₁-C₆haloalkyl, hydroxy C₁-C₆haloalkyl,C₁-C₆alkoxy C₁-C₆haloalkyl, C₁-C₆haloalkoxy C₁-C₆haloalkyl,C₃-C₈halocycloalkyl, C₁-C₆haloalkoxy, C₁-C₃haloalkoxy C₁-C₃haloalkoxy,C₁-C₆haloalkylthio, C₁-C₆haloalkylsulfinyl or C₁-C₆haloalkylsulfonyl,X² is halogen atom, cyano, nitro, C₁-C₆alkyl, C₁-C₆haloalkyl, —OR⁵,—OSO₂R⁵ or —S(O)_(r)R⁵, when m1 is 2, each X² may be identical with ordifferent from each other,Y is halogen atom, cyano, nitro, C₁-C₄alkyl, C₁-C₄haloalkyl,C₁-C₄alkoxy, C₁-C₄haloalkoxy, C₁-C₆alkylthio, C₁-C₆haloalkylthio,C₁-C₆alkylsulfonyl, C₁-C₆haloalkylsulfonyl, —NHR⁷ or —N(R⁷)R⁶,R³ is C₁-C₆haloalkyl or C₃-C₈halocycloalkyl,R⁵ is C₁-C₆alkyl or C₁-C₆haloalkyl,R⁶ is C₁-C₆alkyl, —CHO, C₁-C₆alkylcarbonyl, C₁-C₆haloalkylcarbonyl,C₁-C₆alkoxycarbonyl, C₁-C₆alkylthiocarbonyl, C₁-C₆alkoxythiocarbonyl,C₁-C₆alkyldithiocarbonyl, C₁-C₆alkylsulfonyl or C₁-C₆haloalkylsulfonyl,R⁷ is hydrogen atom or C₁-C₆alkyl,R is halogen atom, cyano, nitro, —NH₂, halosulfonyloxy,C₁-C₆alkylsulfonyloxy, C₁-C₆haloalkylsulfonyloxy, phenylsulfonyloxy,phenylsulfonyloxy substituted with (Z)_(p1) or —C(O)R^(a),R^(a) is halogen atom, —OH, C₁-C₆alkoxy, 1-pyrazolyl, 1-imidazolyl or1-triazolyl,Z is halogen atom, C₁-C₆alkyl or C₁-C₆haloalkyl, when p1 is an integerof 2 or more, each Z may be identical with or different from each other,m1 is an integer of 0 to 2,n is an integer of 0 or 1,p1 is an integer of 1 or 5, andr is an integer of 0 to 2.(7) 3,5-Bis (substituted aryl) substituted isoxazoline compound or thesalt thereof as set forth in (6), wherein(a) in case where R is halosulfonyloxy, C₁-C₆haloalkylsulfonyloxy,phenylsulfonyloxy or phenylsulfonyloxy substituted with (Z)_(p1), Y ishalogen atom, cyano, nitro, C₁-C₆alkyl, C₁-C₄haloalkyl, C₁-C₄alkoxy,C₁-C₄haloalkoxy, C₁-C₆alkylthio, C₁-C₆haloalkylthio, C₁-C₆alkylsulfonylor C₁-C₆haloalkylsulfonyl,(b) in case where R is —C(O)R^(a), Y is cyano, nitro, C₁-C₆alkyl,C₁-C₄haloalkyl, C₁-C₆haloalkylthio or C₁-C₆haloalkylsulfonyl,(c) in case where, R is halogen atom, cyano, nitro or —NH₂, Y is cyano,C₁-C₆alkyl, C₁-C₆haloalkyl, C₁-C₆haloalkylthio orC₁-C₆haloalkylsulfonyl.(8) 4-Hydroxyiminomethyl substituted benzamide compound of formula (3)or a salt thereof:

whereinA¹ is carbon atom or nitrogen atom,J is hydrogen atom or halogen atom,W is oxygen atom or sulfur atom,Y is halogen atom, cyano, nitro, C₁-C₄alkyl, C₁-C₄haloalkyl,C₁-C₄alkoxy,C₁-C₄haloalkoxy, C₁-C₆alkylsulfonyl, C₁-C₆haloalkylsulfonyl or —N(R⁷)R⁶,R¹ is C₁-C₆alkyl, C₁-C₆alkyl arbitrarily substituted with R¹⁶,C₃-C₆cycloalkyl, E-4, E-5, C₃-C₆alkenyl, C₃-C₆haloalkenyl, C₃-C₆alkynyl,—N(R²⁰)R¹⁹, phenyl substituted with (Z)_(p1), D-8, D-10, D-13 to D-15,D-18, D-21, D-34, D-35, D-47, D-48, D-50 to D-53 or D-54,R² is hydrogen atom, C₁-C₆alkyl, C₁-C₄alkoxy C₁-C₄alkyl, cyanoC₁-C₆alkyl, C₃-C₆alkynyl, —C(O)R⁹ or —C(O)OR⁹,R⁶ is —CHO, C₁-C₆alkylcarbonyl, C₁-C₆haloalkylcarbonyl,C₁-C₆alkoxycarbonyl, C₁-C₆alkylthiocarbonyl, C₁-C₆alkoxythiocarbonyl,C₁-C₆alkyldithiocarbonyl, C₁-C₆alkylsulfonyl or C₁-C₆haloalkylsulfonyl,R⁷ is hydrogen atom or C₁-C₆alkyl,R⁹ is C₁-C₆alkyl, C₁-C₆alkoxy C₁-C₄alkyl, C₁-C₆alkylthio C₁-C₄alkyl,C₃-C₈cycloalkyl, C₃-C₆alkenyl or C₃-C₆alkynyl,R¹⁶ is halogen atom, cyano, C₃-C₆cycloalkyl, C₃-C₆halocycloalkyl,C₁-C₆alkoxy, C₁-C₆haloalkoxy, C₁-C₆alkylsulfonyl,C₁-C₆haloalkylsulfonyl, C₁-C₆alkylcarbonyl, —C(O)OR²⁸, —C(O)NHR²⁹,—C(O)N(R²⁹)R²⁸, —C(S)NH₂, —C(R³¹)═NOH, —C(R³¹)═NOR³⁰, phenyl, phenylsubstituted with (Z)_(p1), D-1 to D-4, D-8 to D-38, D-47 to D-55, E-4 toE-7, E-10, E-11 or E-32,D-1 to D-4, D-8 to D-38, D-47 to D-54 and D-55 are aromatic heterocyclicrings of the following formulae, respectively,

Z is halogen atom, cyano, nitro, C₁-C₆alkyl, C₁-C₆haloalkyl,C₁-C₆alkoxy, C₁-C₆haloalkoxy, C₁-C₆alkylsulfonyl,C₁-C₆haloalkylsulfonyl, C₁-C₆alkoxycarbonyl, —C(O)NH₂,C₁-C₆alkylaminocarbonyl, di(C₁-C₆alkyl)aminocarbonyl, —C(S)NH₂,—S(O)₂NH₂, C₁-C₆alkylaminosulfonyl or di(C₁-C₆alkyl)aminosulfonyl, whenp1, p2, p3 or p4 is an integer of 2 or more, each Z may be identicalwith or different from each other,R¹⁵ is C₁-C₆alkyl, phenyl or phenyl substituted with (Z)_(p1),E-4, E-5, E-10, E-11 or E-32 is a saturated heterocyclic ring of thefollowing formulae, respectively

R¹⁹ is C₁-C₆haloalkyl, —C(O)R²⁸, —C(O)OR²⁸, phenyl, phenyl substitutedwith (Z)_(p1), D-3, D-4, D-21, D-47, D-50, D-51, D-53 or D-54,R²⁰ is hydrogen atom or C₁-C₆alkyl,R²² is C₁-C₄alkyl,R²⁸ is C₁-C₆alkyl, C₁-C₆haloalkyl, C₃-C₆cycloalkyl C₁-C₄alkyl,C₃-C₆cycloalkyl,C₃-C₆alkenyl or C₃-C₆alkynyl,R²⁹ is hydrogen atom or C₁-C₆alkyl,R³⁰ is C₁-C₆alkyl,R³¹ is C₁-C₆alkyl,n is an integer of 0 or 1, with a proviso that n is 1 when R¹ and R² aremethyl at the same time,p1 is an integer of 1 to 5,p2 is an integer of 0 to 4,p3 is an integer of 0 to 3,p4 is an integer of 0 to 2,p5 is an integer of 0 or 1,q2 is an integer of 0 to 3, andq3 is an integer of 0 to 2(9) 4-Hydroxyiminomethyl substituted benzamide compound or the saltthereof as set forth in (8), whereinA¹ is carbon atom,W is oxygen atom,Y is halogen atom, C₁-C₆alkyl or C₁-C₆haloalkyl,R¹ is C₁-C₆alkyl arbitrarily substituted with R¹⁶, C₃-C₆cycloalkyl, E-4,E-5, C₃-C₆alkenyl, C₃-C₆haloalkenyl, C₃-C₆alkynyl, D-13 to D-15, D-21,D-47, D-48, D-50 to D-53 or D-54,R¹⁶ is halogen atom, cyano, C₃-C₆cycloalkyl, E-4, E-5, E-10,C₁-C₆alkoxy, C₁-C₆haloalkoxy, C₁-C₆alkylsulfonyl,C₁-C₆haloalkylsulfonyl, —C(O)N(R²⁹)R²⁸, D-1, D-8, D-15 to D-17, D-21,D-22, D-28, D-29, D-34, D-35, D-38, D-47, D-50, D-51 or D-53.(10) Substituted alkenylbenzene compound of formula (4):

whereinX¹ is halogen atom, —SF₅, C₁-C₆haloalkyl, hydroxy C₁-C₆haloalkyl,C₁-C₆alkoxy C₁-C₆haloalkyl, C₃-C₈halocycloalkyl, C₁-C₆haloalkoxy,C₁-C₃haloalkoxy C₁-C₃haloalkoxy, C₁-C₆haloalkylthio,C₁-C₆haloalkylsulfinyl orC₁-C₆haloalkylsulfonyl,X³ is hydrogen atom, halogen atom, cyano, nitro, C₁-C₆alkyl,C₁-C₆haloalkyl, C₁-C₆alkoxy or C₁-C₆alkylthio,X⁴ is hydrogen atom, halogen atom, cyano, C₁-C₄alkyl, C₁-C₄alkoxy orC₁-C₄haloalkoxy,

R³ is —C(R^(3a))(R^(3b))R^(3c),

R^(3a) and R^(3b) independently of each other are halogen atom, orR^(3a) and R^(3b) together may form 3- to 6-membered ring together withthe carbon atom bonding them by forming C₂-C₅haloalkylene chain,R^(3c) is hydrogen atom, halogen atom, C₁-C₅alkyl, C₁-C₅haloalkyl,C₁-C₄haloalkoxy or C₁-C₄haloalkylthio, with a proviso that in case whereX¹ is fluorine atom, chlorine atom or trifluoromethyl and both X² and X³are hydrogen atom, in case where both X¹ and X² are fluorine atom and X³is hydrogen atom, and in case where both X¹ and X² are trifluoromethyland X³ is hydrogen atom, R³ is hydrogen atom, chlorine atom, bromineatom, iodine atom, C₁-C₅alkyl, C₁-C₅haloalkyl, C₁-C₄haloalkoxy orC₁-C₄haloalkylthio.(11) The substituted alkenylbenzene compound as set forth in (10),wherein X¹ is halogen atom, —SF₅, C₁-C₆haloalkyl, C₁-C₆haloalkoxy orC₁-C₆haloalkylthio, X³ is hydrogen atom, halogen atom, cyano, nitro,C₁-C₆alkyl, C₁-C₆haloalkyl or C₁-C₆alkoxy,X⁴ is hydrogen atom or halogen atom,R^(3a) and R^(3b) are fluorine atom,R^(3c) is hydrogen atom, fluorine atom, chlorine atom, bromine atom ortrifluoromethyl, with a proviso that in case where X¹ is fluorine atom,chlorine atom or trifluoromethyl and both X³ and X⁴ are hydrogen atom,in case where both X¹ and X³ are fluorine atom and X⁴ is hydrogen atom,and in case where both X¹ and X³ are trifluoromethyl and X⁴ is hydrogenatom, R³ is hydrogen atom, chlorine atom, bromine atom ortrifluoromethyl.(12) A pesticide containing as an active ingredient one or more selectedfrom isoxazoline-substituted benzamide compound and the salt thereof asset forth in (1) to (5).(13) An agrochemical containing as an active ingredient one or moreselected from isoxazoline-substituted benzamide compound and the saltthereof as set forth in (1) to (5).(14) An endo- or ecto-parasiticide for mammals or birds containing as anactive ingredient one or more selected from isoxazoline-substitutedbenzamide compound and the salt thereof as set forth in (1) to (5).(15) An insecticide or acaricide containing as an active ingredient oneor more selected from isoxazoline-substituted benzamide compound and thesalt thereof as set forth in (1) to (5).

Effect of the Invention

The compound according to the present invention has an excellentinsecticidal and acaricidal activity for many agricultural insect pests,spider mites, endo- or ecto-parasiticide for mammals or birds, andexerts a control effect sufficient for pest insects that acquireresistance against exiting insecticides. Further, the compound haslittle adverse affect on mammals, fishes and beneficial insects, and hasa low persistency and a low impact on the environment. Therefore, thepresent invention can provide a useful and novel pesticide.

BEST MODE FOR CARRYING OUT THE INVENTION

Active compounds used as the pesticide in the present invention aregenerally the compounds of formulae (1) to (5) mentioned above, and thecompounds of formulae (6) to (11) mentioned above are novel productionintermediates used for the production of these active compounds. Theseintermediates contain specific compounds themselves having controlactivity against specific pests that can be used as a control agent forthe pest.

In the compounds included in the present invention, some compounds havegeometrical isomers of E-form and Z-form depending on the kind ofsubstituents. The present invention includes these E-forms, Z-forms andmixtures containing E-form and Z-form in an arbitrary proportion. Inaddition, the compounds included in the present invention have opticallyactive forms resulting from the presence of 1 or more asymmetric carbonatoms, and the present invention includes all optically active forms orracemates. Further, in the compounds of formula (1) according to thepresent invention, some compounds wherein R² is hydrogen atom arepresent in tautomer, and the present invention includes thesestructures,

The compounds included in the present invention can be converted to acidaddition salts for example salts of hydrohalide acid such ashydrofluoric acid, hydrochloric acid, hydrobromic acid, hydriodic acidor the like, salts of inorganic acids such as nitric acid, sulfuricacid, phosphoric acid, chloric acid, perchloric acid or the like, saltsof sulfonic acid such as methansulfonic acid, ethansulfonic acid,trufluoromethansulfonic acid, benzene sulfonic acid, p-toluene sulfonicacid or the like, salts of carboxylic acid such as formic acid, aceticacid, propionic acid, trifluoroacetic acid, fumaric acid, tartaric acid,oxalic acid, maleic acid, malic acid, succinic acid, benzoic acid,mandelic acid, ascorbic acid, lactic acid, gluconic acid, citric acid orthe like, or salts of amino acid such as glutamic acid, aspartic acid orthe like, according to a conventional method.

The compounds included in the present invention can be converted tometal salts for example salts of alkali metal such as lithium, sodium,potassium, salts of alkaline earth metal such as calcium, barium,magnesium, or salts of aluminum, according to a conventional method.

Hereinafter, concrete examples of each substituent shown in thespecification are described. In the specification, “n-” means normal,“i-” means iso, “s-” means secondary, and “t-” means tertiary, and “Ph”means phenyl.

Halogen atom in the compounds of the present invention includes fluorineatom, chlorine atom, bromine atom and iodine atom. In the interim, theindication of “halo” in the specification also means these halogenatoms.

In the specification, the indication of “C_(a)-C_(b)alkyl” meansstraight-chain or branched-chain hydrocarbon groups having carbon atomnumber of a to b, and includes for example methyl, ethyl, n-propyl,i-propyl, n-butyl, s-butyl, i-butyl, t-butyl, n-pentyl, 1-methylbutyl,2-methylbutyl, 3-methylbutyl, 1-ethylpropyl, 1,1-dimethylpropyl,1,2-dimethylpropyl, neopentyl, n-hexyl, 1-methylpentyl, 2-methylpentyl,3-methylpentyl, 4-methylpentyl, 1-ethylbutyl, 2-ethylbutyl,1,1-dimethylbutyl, 1,2-dimethylbutyl, 1,3-dimethylbutyl,2,2-dimethylbutyl, 2,3-dimethylbutyl, 3,3-dimethylbutyl,1,1,2-trimethylpropyl, 1,2,2-trimethylpropyl, 1-ethyl-1-methylpropyl,1-ethyl-2-methylpropyl, heptyl, 5-methylhexyl, 2-ethylpentyl, octyl,2-ethylhexyl, nonyl, 2-methyloctyl, decyl, 2-methylnonyl, undecyl,2-methyldecyl, dodecyl and the like. It is selected from the scope ofthe indicated carbon atom number.

In the specification, the indication of “C_(a)-C_(b)haloalkyl” meansstraight-chain or branched-chain hydrocarbon groups having carbon atomnumber of a to b that a hydrogen atom (hydrogen atoms) bonded to carbonatom is (are) arbitrarily substituted with a halogen atom (halogenatoms). In this case, if it is substituted with two or more halogenatoms, these halogen atoms may be identical with or different from eachother. Concrete examples thereof are for example fluoromethyl,chloromethyl, difluoromethyl, dichloromethyl, trifluoromethyl,chlorodifluoromethyl, trichloromethyl, bromodifluoromethyl,2-fluoroethyl, 2-chloroethyl, 2-bromoethyl, 2,2-difluoroethyl,2-chloro-2-fluoroethyl, 2,2-dichloroethyl, 2-bromo-2-fluoroethyl,2-bromo-2-chloroethyl, 2,2,2-trifluoroethyl, 2-chloro-2,2-difluoroethyl,2,2-dichloro-2-fluoroethyl, 2,2,2-trichloroethyl,2-bromo-2,2-difluoroethyl, 2-bromo-2-chloro-2-fluoroethyl,2-bromo-2,2-dichloroethyl, pentafluoroethyl, 2-fluoropropyl,2-chloropropyl, 2-bromopropyl, 2,3-dichloropropyl, 2,3-dibromopropyl,3,3,3-trifluoropropyl, 3-bromo-3,3-difluoropropyl,2,2,3,3-tetrafluoropropyl, 2-chloro-3,3,3-trifluoropropyl,2,2,3,3,3-pentafluoropropyl, 2,2,2-trifluoro-1-trifluoromethylethyl,heptafluoropropyl, 1,2,2,2-tetrafluoro-1-trifluoromethylethyl,2,2,3,3,4,4-hexafluorobutyl, 2,2,3,4,4,4-hexafluorobutyl,2,2,3,3,4,4,4-heptafluorobutyl, nonafluorobutyl,5-chloro-2,2,3,4,4,5,5-heptafluoropentyl, and the like. It is selectedfrom the scope of the indicated carbon atom number.

In the specification, the indication of “cyano C_(a)-C_(b)alkyl” meansstraight-chain or branched-chain alkyl groups having carbon atom numberof a to b that a hydrogen atom (hydrogen atoms) bonded to carbon atom is(are) arbitrarily substituted with a cyano group (cyano groups).Concrete examples thereof are for example cyanomethyl, 1-cyanoethyl,2-cyanoethyl, 2-cyanopropyl, 3-cyanopropyl, 2-cyanobutyl, and the like.It is selected from the scope of the indicated carbon atom number.

In the specification, the indication of “C_(a)-C_(b)cycloalkyl” meanscyclic hydrocarbon groups having carbon atom number of a to b, and canform 3-membered to 6-membered single ring or conjugated ring structure.In addition, each ring may be arbitrarily substituted alkyl group in thescope of the indicated carbon atom number. Concrete examples thereof arefor example cyclopropyl, 1-methylcyclopropyl, 2-methylcyclopropyl,2,2-dimethylcyclopropyl, 2,2,3,3-tetramethylcyclopropyl, cyclobutyl,cyclopentyl, 2-methylcyclopentyl, 3-methylcyclopentyl, cyclohexyl,2-methylcyclohexyl, 3-methylcyclohexyl, 4-methylcyclohexyl,bicyclo[2.2.1]heptan-2-yl and the like. It is selected from the scope ofthe indicated carbon atom number.

In the specification, the indication of “C_(a)-C_(b)halocycloalkyl”means cyclic hydrocarbon groups having carbon atom number of a to b thata hydrogen atom (hydrogen atoms) bonded to carbon atom is (are)arbitrarily substituted with a halogen atom (halogen atoms), and canform 3-membered to 6-membered single ring or conjugated ring structure.In addition, each ring may be arbitrarily substituted alkyl group in thescope of the indicated carbon atom number. The substitution for halogenatom may be in the ring structure moiety, the side chain moiety or bothof them. Further, if it is substituted with two or more halogen atoms,these halogen atoms may be identical with or different from each other.Concrete examples thereof are for example 2,2-dichlorocyclopropyl,2,2-dibromocyclopropyl, 2,2-difluoro-1-methylcyclopropyl,2,2-dichloro-1-methylcyclopropyl, 2,2-dibromo-1-methylcyclopropyl,2,2-dichloro-3,3-dimethylcyclopropyl, 2,2,3,3-tetrafluorocyclobutyl,2-trifluoromethylcyclohexyl, 3-trifluoromethylcyclohexyl,4-trifluoromethylcyclohexyl and the like. It is selected from the scopeof the indicated carbon atom number.

In the specification, the indication of “C_(a)-C_(b)alkenyl” meansstraight-chain or branched-chain unsaturated hydrocarbon groups havingcarbon atom number of a to b and having 1 or more double bonds. Concreteexamples thereof are for example vinyl, 1-propenyl, 1-methylethenyl,2-propenyl, 2-butenyl, 1-methyl-2-propenyl, 2-methyl-2-propenyl,2-methyl-2-butenyl, 3-methyl-2-butenyl, 2-hexenyl, 2-methyl-2-pentenyl,2,4-dimethyl-2,6-heptadienyl, 3,7-dimethyl-2,6-octadienyl, and the like.It is selected from the scope of the indicated carbon atom number.

In the specification, the indication of “C_(a)-C_(b)haloalkenyl” meansstraight-chain or branched-chain unsaturated hydrocarbon groups havingcarbon atom number of a to b and having 1 or more double bonds, which ahydrogen atom (hydrogen atoms) bonded to carbon atom is (are)arbitrarily substituted with a halogen atom (halogen atoms). In thiscase, if it is substituted with two or more halogen atoms, these halogenatoms may be identical with or different from each other. Concreteexamples thereof are for example 2,2-dichlorovinyl, 2-fluoro-2-propenyl,2-chloro-2-propenyl, 2-bromo-2-propenyl, 3-bromo-2-propenyl,3,3-difluoro-2-propenyl, 2,3-dichloro-2-propenyl,3,3-dichloro-2-propenyl, 2,3-dibromo-2-propenyl,2,3,3-trifluoro-2-propenyl, 1-trifluoromethylvinyl,2,3,3-trichloro-2-propenyl, 2-bromo-2-butenyl,3-bromo-2-methyl-2-propenyl, 4,4-difluoro-3-butenyl,3,4,4-trifluoro-3-butenyl, 3-chloro-4,4,4-trifluoro-2-butenyl, and thelike. It is selected from the scope of the indicated carbon atom number.

In the specification, the indication of “C_(a)-C_(b)cycloalkenyl” meanscyclic unsaturated hydrocarbon groups having carbon atom number of a tob and having 1 or more double bonds, and can form 3-membered to6-membered single ring or conjugated ring structure. In addition, eachring may be arbitrarily substituted alkyl group in the scope of theindicated carbon atom number, and further the double bond may be eitherendo- or exo-form. Concrete examples thereof are for example2-cyclopenten-1-yl, 3-cyclopenten-1-yl, 2-cyclohexen-1-yl,3-cyclohexen-1-yl, bicyclo[2.2.1]-5-hepten-2-yl and the like. It isselected from the scope of the indicated carbon atom number.

In the specification, the indication of “C_(a)-C_(b)halocycloalkenyl”means cyclic unsaturated hydrocarbon groups having carbon atom number ofa to b and having 1 or more double bonds, which a hydrogen atom(hydrogen atoms) bonded to carbon atom is (are) arbitrarily substitutedwith a halogen atom (halogen atoms), and can form 3-membered to6-membered single ring or conjugated ring structure. In addition, eachring may be arbitrarily substituted alkyl group in the scope of theindicated carbon atom number, and further the double bond may be eitherendo- or exo-form. The substitution for halogen atom may be in the ringstructure moiety, the side chain moiety or both of them. Further, if itis substituted with two or more halogen atoms, these halogen atoms maybe identical with or different from each other. Concrete examplesthereof are for example 2-chlorobicyclo[2.2.1]-5-hepten-2-yl and thelike. It is selected from the scope of the indicated carbon atom number.

In the specification, the indication of “C_(a)-C_(b)alkynyl” meansstraight-chain or branched-chain unsaturated hydrocarbon groups havingcarbon atom number of a to b and having 1 or more triple bonds. Concreteexamples thereof are for example ethynyl, 1-propynyl, 2-propynyl,1-methyl-2-propynyl, 2-butynyl, 2-pentynyl, 1-methyl-2-butynyl,2-hexynyl, and the like. It is selected from the scope of the indicatedcarbon atom number.

In the specification, the indication of “C_(a)-C_(b)haloalkynyl” meansstraight-chain or branched-chain unsaturated hydrocarbon groups havingcarbon atom number of a to b and having 1 or more triple bonds, which ahydrogen atom (hydrogen atoms) bonded to carbon atom is (are)arbitrarily substituted with a halogen atom (halogen atoms). In thiscase, if it is substituted with two or more halogen atoms, these halogenatoms may be identical with or different from each other. Concreteexamples thereof are for example 2-chloroethynyl, 2-bromoethynyl,2-iodoethynyl, 3-chloro-2-propynyl, 3-bromo-2-propynyl,3-iodo-2-propynyl, and the like. It is selected from the scope of theindicated carbon atom number.

In the specification, the indication of “C_(a)-C_(b)alkoxy” meansalkyl-O— groups wherein the alkyl has carbon atom number of a to b, andincludes for example methoxy, ethoxy, n-propyloxy, i-propyloxy,n-butyloxy, s-butyloxy, i-butyloxy, t-butyloxy, n-pentyloxy, n-hexyloxyand the like. It is selected from the scope of the indicated carbon atomnumber.

In the specification, the indication of “C_(a)-C_(b)haloalkoxy” meanshaloalkyl-O— groups wherein the haloalkyl has carbon atom number of a tob, and includes for example difluoromethoxy, trifluoromethoxy,chlorodifluoromethoxy, bromodifluoromethoxy, 2-fluoroethoxy,2-chloroethoxy, 2,2,2-trifluoroethoxy, 1,1,2,2-tetrafluoroethoxy,2-chloro-1,1,2-trifluoroethoxy, 2-bromo-1,1,2-trifluoroethoxy,2,2-dichloro-1,1,2-trifluoroethoxy, pentafluoroethoxy,2,2,2-trichloro-1,1-difluoroethoxy, 2-bromo-1,1,2,2-tetrafluoroethoxy,2,2,3,3-tetrafluoropropyloxy, 1,1,2,3,3,3-hexafluoropropyloxy,2,2,2-trifluoro-1-trifluoromethylethoxy, heptafluoropropyloxy,2-bromo-1,1,2,3,3,3-hexafluoropropyloxy, and the like. It is selectedfrom the scope of the indicated carbon atom number.

In the specification, the indication of “C_(a)-C_(b)alkylthio” meansalkyl-S— groups wherein the alkyl has carbon atom number of a to b, andincludes for example methylthio, ethylthio, n-propylthio, i-propylthio,n-butylthio, s-butylthio, i-butylthio, t-butylthio, n-pentylthio,n-hexylthio and the like. It is selected from the scope of the indicatedcarbon atom number.

In the specification, the indication of “C_(a)-C_(b)haloalkylthio” meanshaloalkyl-S— groups wherein the haloalkyl has carbon atom number of a tob, and includes for example difluoromethylthio, trifluoromethylthio,bromodifluoromethylthio, 2,2,2-trifluoroethylthio,1,1,2,2-tetrafluoroethylthio, 1,1,2-trifluoro-2-chloroethylthio,pentafluoroethylthio, 2-bromo-1,1,2,2-tetrafluoroethylthio,heptafluoropropylthio, 1,2,2,2-tetrafluoro-1-trifluoromethylthio,1,2,2,2-tetrafluoro-1-trifluoroethylthio, nonafluorobutylthio, and thelike. It is selected from the scope of the indicated carbon atom number.

In the specification, the indication of “C_(a)-C_(b)alkylsulfinyl” meansalkyl-S(O)— groups wherein the alkyl has carbon atom number of a to b,and includes for example methylsulfinyl, ethylsulfinyl,n-propylsulfinyl, i-propylsulfinyl, n-butylsulfinyl, s-butylsulfinyl,i-butylsulfinyl, t-butylsulfinyl, and the like. It is selected from thescope of the indicated carbon atom number.

In the specification, the indication of “C_(a)-C_(b)haloalkylsulfinyl”means haloalkyl-S(O)— groups wherein the haloalkyl has carbon atomnumber of a to b, and includes for example difluoromethylsulfinyl,trifluoromethylsulfinyl, bromodifluoromethylsulfinyl,2,2,2-trifluoroethylsulfinyl, 2-bromo-1,1,2,2-tetrafluoroethylsulfinyl,1,2,2,2-tetrafluoro-1-trifluoromethylethylsulfinyl,nonafluorobutylsulfinyl, and the like. It is selected from the scope ofthe indicated carbon atom number.

In the specification, the indication of “C_(a)-C_(b)alkylsulfonyl” meansalkyl-SO₂— groups wherein the alkyl has carbon atom number of a to b,and includes for example methanesulfonyl, ethanesulfonyl,n-propylsulfonyl, i-propylsulfonyl, n-butylsulfonyl, s-butylsulfonyl,i-butylsulfonyl, t-butylsulfonyl, n-pentylsulfonyl, n-hexylsulfonyl, andthe like. It is selected from the scope of the indicated carbon atomnumber.

In the specification, the indication of “C_(a)-C_(b)haloalkylsulfonyl”means haloalkyl-SO₂— groups wherein the haloalkyl has carbon atom numberof a to b, and includes for example difluoromethanesulfonyl,trifluoromethanesulfonyl, chlorodifluoromethanesulfonyl,bromodifluoromethanesulfonyl, 2,2,2-trifluoroethanesulfonyl,1,1,2,2-tetrafluoroethanesulfonyl,1,1,2-trifluoro-2-chloroethanesulfonyl, and the like. It is selectedfrom the scope of the indicated carbon atom number.

In the specification, the indication of “C_(a)-C_(b)alkylamino” meansamino groups, which either hydrogen atom is substituted with theabove-mentioned alkyl group having carbon atom number of a to b, andincludes for example methylamino, ethylamino, n-propylamino,i-propylamino, n-butylamino, i-butylamino, t-butylamino, and the like.It is selected from the scope of the indicated carbon atom number.

In the specification, the indication of “di(C_(a)-C_(b)alkyl)amino”means amino groups, which both hydrogen atoms are substituted with theabove-mentioned alkyl groups having carbon atom number of a to b thatmay be identical with or different from each other, and includes forexample dimethylamino, ethyl(methyl)amino, diethylamino,n-propyl(methyl)amino, i-propyl(methyl)amino, di(n-propyl)amino,n-butyl(methyl)amino, i-butyl(methyl)amino, t-butyl(methyl)amino, andthe like. It is selected from the scope of the indicated carbon atomnumber.

In the specification, the indication of “C_(a)-C_(b)alkylcarbonyl” meansalkyl-C(O)— groups wherein the alkyl has carbon atom number of a to b,and includes for example CH₃C(O)—, CH₃CH₂C(O)—, CH₃CH₂CH₂C(O)—,(CH₃)₂CHC(O)—, CH₃(CH₂)₃C(O)—, (CH₃)₂CHCH₂C(O)—, CH₃CH₂CH(CH₃)C(O)—,(CH₃)₃CC(O)—, CH₃(CH₂)₄C(O)—, CH₃(CH₂)₅C(O)—, and the like. It isselected from the scope of the indicated carbon atom number.

In the specification, the indication of “C_(a)-C_(b)haloalkylcarbonyl”means haloalkyl-C(O)— groups wherein the haloalkyl has carbon atomnumber of a to b, and includes for example FCH₂C(O)—, ClCH₂C(O)—,F₂CHC(O)—, Cl₂CHC(O)—, CF₃C(O)—, ClCF₂C(O)—, BrCF₂C(O)—, CCl₃C(O)—,CF₃CF₂C(O)—, ClCH₂CH₂CH₂C(O)—, CF₃CF₂CF₂C(O)—, ClCH₂C(CH₃)₂C(O)—, andthe like. It is selected from the scope of the indicated carbon atomnumber.

In the specification, the indication of “C_(a)-C_(b)alkoxycarbonyl”means alkyl-O—C(O)— groups wherein the alkyl has carbon atom number of ato b, and includes for example CH₃OC(O)—, CH₃CH₂OC(O)—, CH₃CH₂CH₂OC(O)—,(CH₃)₂CHOC(O)—, CH₃(CH₂)₃OC(O)—, (CH₃)₂CHCH₂OC(O)—, (CH₃)₃COC(O)—, andthe like. It is selected from the scope of the indicated carbon atomnumber.

In the specification, the indication of “C_(a)-C_(b)haloalkoxycarbonyl”means haloalkyl-O—C(O)— groups wherein the haloalkyl has carbon atomnumber of a to b, and includes for example ClCH₂CH₂OC(O)—, CF₃CH₂OC(O)—,and the like. It is selected from the scope of the indicated carbon atomnumber.

In the specification, the indication of “C_(a)-C_(b)alkylaminocarbonyl”means carbamoyl groups, which either hydrogen atom is substituted withthe above-mentioned alkyl group having carbon atom number of a to b, andincludes for example CH₃NHC(O)—, CH₃CH₂NHC(O)—, CH₃CH₂CH₂NHC(O)—,(CH₃)₂CHNHC(O)—, CH₃(CH₂)₃NHC(O)—, (CH₃)₂CHCH₂NHC(O)—,CH₃CH₂CH(CH₃)NHC(O)—, (CH₃)₃CNHC(O)—, and the like. It is selected fromthe scope of the indicated carbon atom number.

In the specification, the indication of“C_(a)-C_(b)haloalkylaminocarbonyl” means carbamoyl groups, which eitherhydrogen atom is substituted with the above-mentioned haloalkyl grouphaving carbon atom number of a to b, and includes for example2-fluoroethylcarbamoyl, 2-chloroethylcarbamoyl, 2,2-difluorocarbamoyl,2,2,2-trifluoroethylcarbamoyl, and the like. It is selected from thescope of the indicated carbon atom number.

In the specification, the indication of“di(C_(a)-C_(b)alkyl)aminocarbonyl” means carbamoyl groups, which bothhydrogen atoms are substituted with the above-mentioned alkyl grouphaving carbon atom number of a to b that may be identical with ordifferent from each other, and includes for example (CH₃)₂NC(O)—,CH₃CH₂N(CH₃)C(O)—, (CH₃CH₂)₂NC(O)—, (CH₃CH₂CH₂)₂NC(O)—,(CH₃CH₂CH₂CH₂)₂NC(O)—, and the like. It is selected from the scope ofthe indicated carbon atom number.

In the specification, the indication of “C_(a)-C_(b)alkylaminosulfonyl”means sulfamoyl groups, which either hydrogen atom is substituted withthe above-mentioned alkyl group having carbon atom number of a to b, andincludes for example CH₃NHSO₂—, CH₃CH₂NHSO₂—, CH₃CH₂CH₂NHSO₂—,(CH₃)₂CHNHSO₂—, CH₃(CH₂)₃NHSO₂—, (CH₃)₂CHCH₂NHSO₂—, CH₃CH₂CH(CH₃)NHSO₂—,(CH₃)₃CNHSO₂, and the like. It is selected from the scope of theindicated carbon atom number.

In the specification, the indication of“di(C_(a)-C_(b)alkyl)aminosulfonyl” means sulfamoyl groups, which bothhydrogen atoms are substituted with the above-mentioned alkyl grouphaving carbon atom number of a to b that may be identical with ordifferent from each other, and includes for example (CH₃)₂NSO₂—,CH₃CH₂N(CH₃)SO₂—, (CH₃CH₂)₂NSO₂—, (CH₃CH₂CH₂)₂NSO₂—,(CH₃CH₂CH₂CH₂)₂NSO₂—, and the like. It is selected from the scope of theindicated carbon atom number.

In the specification, the indication of “tri(C_(a)-C_(b)alkyl)silyl”means silyl groups substituted with the above-mentioned alkyl grouphaving carbon atom number of a to b that may be identical with ordifferent from each other, and includes for example trimethylsilyl,triethylsilyl, tri(n-propyl)silyl, ethyldimethylsilyl,n-propyldimethylsilyl, n-butyldimethylsilyl, i-butyldimethylsilyl,t-butyldimethylsilyl, and the like. It is selected from the scope of theindicated carbon atom number.

In the specification, the indication of “C_(a)-C_(b)alkylcarbonyloxy”means alkylcarbonyl-O— groups wherein the alkyl has carbon atom numberof a to b, and includes for example CH₃C(O)—O—, CH₃CH₂C(O)—O—,CH₃CH₂CH₂C(O)—O—, (CH₃)₂CHC(O)—O—, CH₃(CH₂)₃C(O)—O—, (CH₃)₂CHCH₂C(O)—O—,CH₃CH₂CH(CH₃)C(O)—O—, (CH₃)₃CC(O)—O—, and the like. It is selected fromthe scope of the indicated carbon atom number.

In the specification, the indication of “C_(a)-C_(b)alkylsulfonyloxy”means alkylsulfonyl-O— groups wherein the alkyl has carbon atom numberof a to b, and includes for example CH₃SO₂—O—, CH₃CH₂SO₂—O—,CH₃CH₂CH₂SO₂—O—, (CH₃)₂CHSO₂—O—, and the like. It is selected from thescope of the indicated carbon atom number.

In the specification, the indication of“C_(a)-C_(b)haloalkylsulfonyloxy” means haloalkylsulfonyl-O— groupswherein the haloalkyl has carbon atom number of a to b, and includes forexample difluoromethanesulfonyl-O—, trifluoromethanesulfonyl-O—,chlorodifluoromethanesulfonyl-O—, bromodifluoromethanesulfonyl-O—, andthe like. It is selected from the scope of the indicated carbon atomnumber.

In the specification, the indication of “C_(a)-C_(b)cycloalkylC_(d)-C_(e)alkyl”, “C_(a)-C_(b)halocycloalkyl C_(d)-C_(e)alkyl”,“C_(a)-C_(b)alkoxy C_(d)-C_(e)alkyl”, “C_(a)-C_(b)haloalkoxyC_(d)-C_(e)alkyl”, “C_(a)-C_(b)alkylthio C_(d)-C_(e)alkyl”,“C_(a)-C_(b)haloalkylthio C_(d)-C_(e)alkyl”, “C_(a)-C_(b)alkylsulfinylC_(d)-C_(e)alkyl”, “C_(a)-C_(b)haloalkylsulfinyl C_(d)-C_(e)alkyl”,“C_(a)-C_(b)alkylsulfonyl C_(d)-C_(e)alkyl”,“C_(a)-C_(b)haloalkylsulfonyl C_(d)-C_(e)alkyl”,“C_(a)-C_(b)alkoxycarbonyl C_(d)-C_(e)alkyl”, “phenyl C_(d)-C_(e)alkyl”or “phenyl C_(d)-C_(e)alkyl substituted with (Z)_(p1)” meansstraight-chain or branched-chain hydrocarbon groups having carbon atomnumber of d to e, which a hydrogen atom (hydrogen atoms) bonded tocarbon atom is (are) arbitrarily substituted with theC_(a)-C_(b)cycloalkyl, C_(a)-C_(b)halocycloalkyl, C_(a)-C_(b)alkoxy,C_(a)-C_(b)haloalkoxy, C_(a)-C_(b)alkylthio, C_(a)-C_(b)haloalkylthio,C_(a)-C_(b)alkylsulfinyl, C_(a)-C_(b)haloalkylsulfinyl,C_(a)-C_(b)alkylsulfonyl, C_(a)-C_(b)haloalkylsulfonyl,C_(a)-C_(b)alkoxycarbonyl, phenyl or phenyl substituted with (Z)_(p1)that has the meaning mentioned above, respectively. It is selected fromthe scope of the indicated carbon atom number.

In the specification, the indication of “C_(a)-C_(b)alkyl arbitrarilysubstituted with R⁴”, “C_(a)-C_(b)alkyl arbitrarily substituted withR¹⁶”, “C_(a)-C_(b)alkyl arbitrarily substituted with R²⁴”,“C_(a)-C_(b)alkyl arbitrarily substituted with R³²”, or“C_(a)-C_(b)alkyl arbitrarily substituted with R³⁵” means straight-chainor branched-chain hydrocarbon groups having carbon atom number of d toe, which a hydrogen atom (hydrogen atoms) bonded to carbon atom is (are)arbitrarily substituted with R⁴, R¹⁶, R²⁴, R³² or R³⁵. It is selectedfrom the scope of the indicated carbon atom number.

In this case, when two or more substituents R⁴, R¹⁶, R²⁴, R³² or R³⁵ arepresent on the C_(a)-C_(b)alkyl, respective R⁴, R¹⁶, R²⁴, R³² or R³⁵ maybe identical with or different from each other.

In the specification, the indication of “hydroxy C_(d)-C_(e)cycloalkyl”,“C_(a)-C_(b)alkoxy C_(d)-C_(e)cycloalkyl”, “C_(a)-C_(b)alkenylC_(d)-C_(e)cycloalkyl” or “C_(a)-C_(b)haloalkenyl C_(d)-C_(e)cycloalkyl”means the cycloalkyl having carbon atom number of d to e, which ahydrogen atom (hydrogen atoms) bonded to carbon atom is (are)arbitrarily substituted with C_(a)-C_(b)alkoxy, C_(a)-C_(b)alkenyl,C_(a)-C_(b)haloalkenyl or hydroxy. It is selected from the scope of theindicated carbon atom number.

In the specification, the indication of “C_(a)-C_(b)cycloalkylarbitrarily substituted with R⁴”, “C_(a)-C_(b)cycloalkyl arbitrarilysubstituted with R¹⁶”, “C_(a)-C_(b)cycloalkyl arbitrarily substitutedwith R²⁴” or “C_(a)-C_(b)cycloalkyl arbitrarily substituted with R³²”means the cycloalkyl groups having carbon atom number of a to b, which ahydrogen atom (hydrogen atoms) bonded to carbon atom is (are)arbitrarily substituted with R⁴, R¹⁶, R²⁴ or R³². The substitution forR⁴, R¹⁶, R²⁴ or R³² may be in the ring structure moiety, the side chainmoiety or both of them. In this case, when two or more substituents R⁴,R¹⁶, R²⁴ or R³² are present on the C_(a)-C_(b)cycloalkyl, respective R⁴,R¹⁶, R²⁴ or R³² may be identical with or different from each other.

In the specification, the indication of “phenyl C_(a)-C_(b)alkenyl” or“phenyl C_(a)-C_(b)alkenyl substituted with (Z)_(p1)” means the alkenylhaving carbon atom number of a to b, which a hydrogen atom (hydrogenatoms) bonded to carbon atom is (are) arbitrarily substituted phenyl orphenyl substituted with (Z)_(p1). It is selected from the scope of theindicated carbon atom number.

In the specification, the indication of “C_(a)-C_(b)alkenyl arbitrarilysubstituted with R⁴”, “C_(a)-C_(b)alkenyl arbitrarily substituted withR¹⁶”, “C_(a)-C_(b)alkenyl arbitrarily substituted with R²⁴” or“C_(a)-C_(b)alkenyl arbitrarily substituted with R³²” means the alkenylgroups having carbon atom number of a to b, which a hydrogen atom(hydrogen atoms) bonded to carbon atom is (are) arbitrarily substitutedwith R⁴, R¹⁶, R²⁴ or R³². It is selected from the scope of the indicatedcarbon atom number. In this case, when two or more substituents R⁴, R¹⁶,R²⁴ or R³² are present on the C_(a)-C_(b)alkenyl, respective R⁴, R¹⁶,R²⁴ or R³² may be identical with or different from each other.

In the specification, the indication of “phenyl C_(a)-C_(b)alkynyl” or“phenyl C_(a)-C_(b)alkynyl substituted with (Z)_(p1)” means the alkynylhaving carbon atom number of a to b, which a hydrogen atom (hydrogenatoms) bonded to carbon atom is (are) arbitrarily substituted phenyl orphenyl substituted with (Z)_(p1). It is selected from the scope of theindicated carbon atom number.

In the specification, the indication of “C_(a)-C_(b)alkynyl arbitrarilysubstituted with R⁴”, “C_(a)-C_(b)alkynyl arbitrarily substituted withR¹⁶”, “C_(a)-C_(b)alkynyl arbitrarily substituted with R²⁴” or“C_(a)-C_(b)alkynyl arbitrarily substituted with R³²” means the alkynylgroups having carbon atom number of a to b, which a hydrogen atom(hydrogen atoms) bonded to carbon atom is (are) arbitrarily substitutedwith R⁴, R¹⁶, R²⁴ or R³². It is selected from the scope of the indicatedcarbon atom number. In this case, when two or more substituents R⁴, R¹⁶,R²⁴ or R³² are present on the C_(a)-C_(b)alkenyl, respective R⁴, R¹⁶,R²⁴ or R³² may ma be identical with or different from each other.

In the specification, concrete examples of the indication of “R¹ and R²together may form 3- to 8-membered ring together with the nitrogen atombonding them by forming C₂ to C₇ alkylene chain, in this case, thealkylene chain may contain one oxygen atom, sulfur atom or nitrogenatom”,

“R¹⁰ together with R⁹ may form 3- to 7-membered ring with the nitrogenatom bonding them by forming C₂-C₆alkylene chain, in this case, thealkylene chain may contain one oxygen atom, sulfur atom or nitrogenatom”,“R¹⁸ together with R¹⁷ may form 5- to 8-membered ring with the nitrogenatom bonding them by forming C₄-C₇alkylene chain, in this case, thealkylene chain may contain one oxygen atom or sulfur atom”,“R²⁶ together with R²⁵ may form 3- to 6-membered ring with the nitrogenatom bonding them by forming C₂-C₅alkylene chain, in this case, thealkylene chain may contain one oxygen atom or sulfur atom”,“R²⁹ together with R²⁸ may form 3- to 6-membered ring with the nitrogenatom bonding them by forming C₂-C₅alkylene chain, in this case, thealkylene chain may contain one oxygen atom, sulfur atom or nitrogenatom”,“R³⁴ together with R³³ may form 3- to 6-membered ring with the nitrogenatom bonding them by forming C₂-C₅alkylene chain, in this case, thealkylene chain may contain one oxygen atom or sulfur atom”,are for example aziridine, azetidine, pyrrolidine, oxazolidine,thiazoridine, imidazolidine, piperidine, morpholine, thiomorpholine,piperazine, homopiperidine, heptamethyleneimine, and the like. It isselected from the scope of the indicated carbon atom number.

In the specification, concrete examples of the indication of “R⁷together with R⁶ may form 3- to 7-membered ring with the nitrogen atombonding them by forming C₂-C₆alkylene chain, in this case, the alkylenechain may contain one oxygen atom, sulfur atom or nitrogen atom” are forexample aziridine, azetidine, azetidin-2-one, pyrrolidine,pyrrolidin-2-one, oxazolidine, oxazolidin-2-one, thiazoridine,thiazoridin-2-one, imidazolidine, imidazolidin-2-one, piperidine,piperidin-2-one, morpholine, tetrahydro-1,3-oxadin-2-one,thiomorpholine, tetrahydro-1,3-thiazin-2-one, piperazine,tetrahydropyrimidin-2-one, homopiperidine, homopiperidin-2-one, and thelike. It is selected from the scope of the indicated carbon atom number.

In the specification, concrete examples of the indication of “R¹¹together with R⁹ may form 5- to 7-membered ring with the atom bondingthem by forming C₂-C₄alkylene chain, in this case, the alkylene chainmay contain one oxygen atom, sulfur atom or nitrogen atom” are forexample isoxazoline, oxazoline, thiazoline, imidazoline,1,4,2-dioxazoline, 1,4,2-oxathiazoline, 1,2,4-oxadiazoline,dihydro-1,2-oxadine, dihydro-1,3-oxadine, dihydro-1,3-thiazine,3,4,5,6-tetrahydropyrimidine, dihydro-1,4,2-dioxadine,dihydro-1,4,2-oxathiazine, dihydro-4H-1,2,4-oxadiazine,tetrahydro-1,2-oxazepine, and the like. It is selected from the scope ofthe indicated carbon atom number.

In the specification, concrete examples of the indication of “R³¹together with R³⁹ may form 5- to 7-membered ring with the atom bondingthem by forming C₂-C₄alkylene chain, in this case, the alkylene chainmay contain one oxygen atom, sulfur atom or nitrogen atom” are forexample oxazoline, thiazoline, imidazoline, dihydro-1,3-oxazine,dihydro-1,3-thiazine, 3,4,5,6-tetrahydropyrimidine,dihydro-1,4,2-dioxadine, and the like. It is selected from the scope ofthe indicated carbon atom number.

In the compounds included in the present invention, the combination ofthe atoms of A¹, A² and A³ includes for example the following groups.

That is, A-I: A¹, A² and A³ are carbon atoms.A-II: A¹ is nitrogen atom, A² and A³ are carbon atoms.A-III: A² is nitrogen atom, A¹ and A³ are carbon atoms.A-IV: A¹ and A³ are nitrogen atom, A² is carbon atom.A-V: A² and A³ are nitrogen atom, A¹ is carbon atom.

In the compounds included in the present invention, the substituent Gincludes for example aromatic 6-membered rings shown in any one of G-1to G-10 and aromatic 5-membered rings shown in any one of G-11 to G-25.Among them, aromatic 6-membered rings shown in G-1, G-3 and G-4 andaromatic 5-membered rings shown in any one of G-13, G-14, G-17, G-18,G-20, G-21 and G-22 are preferable, and aromatic 6-membered ring shownin G-1 is particularly preferable.

In the compounds included in the present invention, the substituent Wincludes for example oxygen atom or sulfur atom.

In the compounds included in the present invention, the substituent Xincludes for example the following groups. In each case mentioned below,when m is an integer of 2 or more, Xs may be identical with or differentfrom each other.

That is, X-I: halogen atom and C₁-C₆haloalkyl.X-II: halogen atom, C₁-C₆alkyl, C₁-C₆haloalkyl, C₁-C₆alkoxy,C₁-C₆alkylsulfonyloxy, C₁-C₆alkylthio, C₁-C₆alkylsulfinyl andC₁-C₆alkylsulfonyl.X-III: halogen atom, C₁-C₆haloalkyl, C₁-C₆haloalkoxy, C₁-C₃haloalkoxyC₁-C₃haloalkoxy, C₁-C₆haloalkylsulfonyloxy, C₁-C₆haloalkylthio,C₁-C₆haloalkylsulfinyl and C₁-C₆haloalkylsulfonyl.X-IV: halogen atom, C₁-C₆haloalkyl, cyano, nitro, —SF₅ and—Si(R¹³)(R¹⁴)R¹² wherein R¹² is C₁-C₆alkyl, phenyl or phenyl substitutedwith (Z)_(p1), R¹³ and R¹⁴ independently of each other are C₁-C₆alkyl.X-V: halogen atom and C₁-C₆alkyl arbitrarily substituted with R⁴ whereinR⁴ is halogen atom, cyano, —OH, C₁-C₆alkoxy, C₁-C₆haloalkoxy,C₁-C₆alkylthio, C₁-C₆haloalkylthio, C₁-C₆alkylsulfinyl,C₁-C₆haloalkylsulfinyl, C₁-C₆alkylsulfonyl, C₁-C₆haloalkylsulfonyl ortri(C₁-C₆alkyl)silyl.X-VI: halogen atom, C₁-C₆haloalkyl, C₃-C₈cycloalkyl,C₃-C₈halocycloalkyl, C₂-C₆alkenyl, C₂-C₆haloalkenyl, C₂-C₆alkynyl,C₂-C₆haloalkynyl, E-10, E-12, E-18, E-32, E-35 and E-43.X-VII: halogen atom, C₁-C₆haloalkyl, —OR⁵, —OSO₂R⁵ and —S(O)_(r)R⁵wherein R⁵ is C₁-C₆alkyl, C₁-C₆haloalkyl, C₁-C₃haloalkoxyC₁-C₃haloalkyl, C₃-C₈cycloalkyl, C₃-C₈halocycloalkyl, C₂-C₆alkenyl,C₂-C₆haloalkenyl, C₃-C₆alkynyl, C₃-C₆haloalkynyl, E-4 to E-9, E-23 toE-27 or E-28, r is an integer of 0 to 2.X-VIII: halogen atom, C₁-C₆haloalkyl, —C(O)OR⁹, —C(O)SR⁹, —C(S)OR⁹,—C(S)SR⁹, —C(S)NHR¹⁰, —C(S)N(R¹⁰)R⁹, —CH═NOR¹¹ and —C(R⁹)═NOR¹¹ whereinR⁹ is C₁-C₆alkyl, C₁-C₆haloalkyl, C₃-C₈cycloalkyl orC₃-C₈halocycloalkyl, R¹⁰ is hydrogen atom or C₁-C₆alkyl, or R¹⁰ togetherwith R⁹ may form 5- or 6-membered ring with the nitrogen atom bondingthem by forming C₄-C₅alkylene chain, in this case, the alkylene chainmay contain one oxygen atom or sulfur atom, R¹¹ is C₁-C₆alkyl orC₁-C₆haloalkyl, or R¹¹ together with R⁹ may form 5- or 6-membered ringwith the atom bonding them by forming C₂-C₃alkylene chain, in this case,the alkylene chain may be arbitrarily substituted with C₁-C₆alkyl.X-IX: m is 2, two adjacent Xs form 5- or 6-membered ring with the carbonatom bonding them by forming —CF₂OCF₂—, —OCF₂O—, —CF₂OCF₂O— or—OCF₂CF₂O—.

In the compounds included in the present invention, m indicating thenumber of substituent X is an integer of 0 to 5. Among them, m ispreferably 1, 2 and 3.

In the compounds included in the present invention, the substituent Yincludes for example the following groups. In each case mentioned below,when n is an integer of 2 or more, Ys may be identical with or differentfrom each other.

That is, Y-I: halogen atom, C₁-C₆alkyl and C₁-C₆haloalkyl.Y-II: halogen atom, C₁-C₆alkyl, cyano, nitro, —C(O)NH₂ and —C(S)NH₂.Y-III: halogen atom, C₁-C₆alkyl and C₁-C₆alkyl arbitrarily substitutedwith C₁-C₆alkyl and R⁴ wherein R⁴ is halogen atom, cyano, —OH,C₁-C₆alkoxy, C₁-C₆haloalkoxy, C₁-C₆alkylthio, C₁-C₆haloalkylthio,C₁-C₆alkylsulfinyl, C₁-C₆haloalkylsulfinyl, C₁-C₆alkylsulfonyl,C₁-C₆haloalkylsulfonyl or tri(C₁-C₆alkyl)silyl.Y-IV: halogen atom, C₁-C₆alkyl, —OR⁵, —OSO₂R⁵ and —S(O)_(r)R⁵ wherein R⁵is C₁-C₆alkyl, C₁-C₆haloalkyl, C₁-C₃haloalkoxy C₁-C₃haloalkyl,C₃-C₈cycloalkyl, C₃-C₈halocycloalkyl, C₂-C₆alkenyl, C₂-C₆haloalkenyl,C₃-C₆alkynyl, C₃-C₆haloalkynyl, E-4 to E-9, E-23 to E-27 or E-28, r isan integer of 0 to 2.Y-V: halogen atom, C₁-C₆alkyl, —NHR⁷, —N(R⁷)R⁶ wherein R⁶ is C₁-C₆alkyl,C₁-C₆haloalkyl, —S(O)₂R⁹, —CHO, —C(O)R⁹, —C(O)OR⁹, —C(O)SR⁹, —C(S)OR⁹ or—C(S)SR⁹, R⁷ is hydrogen atom, C₁-C₆alkyl or C₁-C₆haloalkyl, R⁹ isC₁-C₆alkyl, C₁-C₆haloalkyl, C₃-C₈cycloalkyl or C₃-C₈halocycloalkyl and—N═C(R⁹)OR⁸ wherein R⁸ is C₁-C₆alkyl, R⁹ is C₁-C₆alkyl orC₁-C₆haloalkyl.Y-VI: halogen atom, nitro, C₁-C₆alkyl, C₁-C₆haloalkyl, C₁-C₆alkylthio,C₁-C₆alkylamino and di(C₁-C₆alkyl)amino.

In the compounds included in the present invention, n indicating thenumber of substituent Y is an integer of 0 to 4. Among them, n ispreferably 0 and 1.

In the compounds included in the present invention, the substituent R¹includes for example the following groups.

That is, R¹-I: C₁-C₆alkyl, C₁-C₆alkyl arbitrarily substituted with R¹⁶(wherein R¹⁶ is halogen atom, C₃-C₆cycloalkyl, C₃-C₆halocycloalkyl,phenyl, phenyl substituted with (Z)_(p1), D-1 to D-4, D-8 to D-38, D-47to D-55, E-4 to E-12, E-18, E-19, E-32, E-35, E-43, M-2, M-3, M-5, M-8,M-9 or M-10), C₃-C₈cycloalkyl and C₃-C₈halocycloalkyl.R¹-II: C₁-C₆alkyl arbitrarily substituted with —OR²⁵ wherein R²⁵ isC₁-C₆alkyl, C₁-C₆haloalkyl, C₁-C₆alkylcarbonyl, C₁-C₆alkoxycarbonyl,C₁-C₆alkylaminocarbonyl, di(C₁-C₆alkyl)aminocarbonyl orC₁-C₆alkylsulfonyl.R¹-III: C₁-C₆alkyl arbitrarily substituted with —N(R²⁶)R²⁵ wherein R²⁵is C₁-C₆alkyl, C₁-C₆haloalkyl, C₁-C₆alkylcarbonyl, C₁-C₆alkoxycarbonyl,C₁-C₆alkylaminocarbonyl, di(C₁-C₆alkyl)aminocarbonyl orC₁-C₆alkylsulfonyl, R²⁶ is hydrogen or C₁-C₆alkyl.R¹-IV: C₁-C₆alkyl arbitrarily substituted with —S(O)_(r)R²⁷ wherein R²⁷is C₁-C₆alkyl, C₁-C₆haloalkyl or tri(C₁-C₄alkyl)silyl C₁-C₄alkyl, r isan integer of 0 to 2.R¹-V: C₁-C₆alkyl arbitrarily substituted with R¹⁶ wherein R¹⁶ is cyano,—C(O)R²⁸, —C(O)OR²⁸, —C(O)NHR²⁹, —C(O)N(R²⁹)R²⁸, —C(O)N(R²⁹)OR²⁸,—C(S)NHR²⁹, —C(S)N(R²⁹)R²⁸, —SO₂NHR²⁹, —SO₂N(R²⁹)R²⁸, —C(R³¹)═NOH,—C(R³¹)═NOR³⁰, —C(═NR³¹)OR³⁰ or —C(═NR³¹)SR³⁰, R²⁸ is C₁-C₆alkyl,C₁-C₆haloalkyl, C₃-C₆cycloalkyl C₁-C₄alkyl, C₁-C₆alkoxy C₁-C₄alkyl,C₁-C₆alkylthio C₁-C₄alkyl, cyano C₁-C₆alkyl, phenyl C₁-C₄alkyl, phenylC₁-C₄alkyl substituted with (Z)_(p1), C₃-C₆cycloalkyl, C₃-C₆alkenyl,C₃-C₆haloalkenyl, C₃-C₆alkynyl, phenyl or phenyl substituted with(Z)_(p1), R²⁹ is hydrogen atom, C₁-C₆alkyl, C₃-C₆alkenyl orC₃-C₆alkynyl, R³⁰ is C₁-C₆alkyl or C₃-C₆cycloalkyl C₁-C₄alkyl, R³¹ ishydrogen atom or C₁-C₆alkyl, or R³¹ together with R³⁰ may for 5- or6-membered ring with the atom bonding them by forming C₂-C₃alkylenechain.R¹-VI: C₃-C₆alkenyl, C₃-C₆haloalkenyl, C₃-C₆alkynyl, C₃-C₆haloalkynyl,phenyl substituted with (Z)_(p1), D-8, D-10, D-11, D-13 to D-15, D-17,D-18, D-21 to D-23, D-26 to D-37, D-39, D-40, D-42, D-45, D-47 to D-54,D-56, D-58, E-4, E-5, E-7 and E-9.R¹-VII: —N(R²⁰)R¹⁹ wherein R¹⁹ is C₁-C₆haloalkyl, C₃-C₆cycloalkyl,—C(O)R²⁸, —C(O)OR²⁸, —C(O)NHR²⁹, —C(O)N(R²⁹)R²⁸, —C(S)NHR²⁹,—C(S)N(R²⁹)R²⁸, phenyl, phenyl substituted with (Z)_(p1), D-3, D-4,D-21, D-47, D-50, D-51, D-53 or D-54, R²⁰ is hydrogen atom, C₁-C₆alkyl,C₁-C₄alkoxy C₁-C₄alkyl, C₁-C₄alkylthio C₁-C₄alkyl, cyano C₁-C₆alkyl,C₃-C₆alkenyl, C₃-C₆alkynyl, —CHO, C₁-C₆alkylcarbonyl,C₁-C₆alkoxycarbonyl or C₁-C₆alkylsulfonyl, R²⁸ is C₁-C₆alkyl,C₁-C₆haloalkyl, C₃-C₆cycloalkyl C₁-C₄alkyl, C₁-C₆alkoxy C₁-C₄alkyl,C₁-C₆alkylthio C₁-C₄alkyl, cyano C₁-C₆alkyl, phenyl C₁-C₄alkyl, phenylC₁-C₄alkyl substituted with (Z)_(p1), C₃-C₆cycloalkyl, C₃-C₆alkenyl,C₃-C₆haloalkenyl, C₃-C₆alkynyl, phenyl or phenyl substituted with(Z)_(p1), R²⁹ is hydrogen atom, C₁-C₆alkyl, C₃-C₆alkenyl orC₃-C₆alkynyl.R¹-VIII: C₁-C₆alkyl, C₁-C₆haloalkyl, C₁-C₆alkyl arbitrarily substitutedwith R¹⁶ (wherein R¹⁶ is cyano, C₃-C₆cycloalkyl, C₃-C₆halocycloalkyl,C₁-C₆alkoxy, C₁-C₆haloalkoxy, C₁-C₆alkylthio, C₁-C₆haloalkylthio,C₁-C₆alkylsulfinyl, C₁-C₆haloalkylsulfinyl, C₁-C₆alkylsulfonyl,C₁-C₆haloalkylsulfonyl, C₁-C₆alkylcarbonyl, —C(O)OR²⁸, —C(O)NHR²⁹,—C(O)N(R²⁹)R²⁸, —C(S)NH₂, —C(R³¹)═NOH, —C(R³¹)═NOR³⁰, phenyl, phenylsubstituted with (Z)_(p1), D-1 to D-4, D-8 to D-38, D-47 to D-55, E-4 toE-7, E-10, E-11 or E-32, R²⁸ is C₁-C₆alkyl, C₁-C₆haloalkyl,C₃-C₆cycloalkyl C₁-C₄alkyl, C₃-C₆cycloalkyl, C₃-C₈alkenyl orC₃-C₈alkynyl, R²⁹ is hydrogen atom or C₁-C₆alkyl, R³⁰ is C₁-C₆alkyl, R³¹is hydrogen or C₁-C₆alkyl), C₃-C₆cycloalkyl, E-4, E-5, C₃-C₆alkenyl,C₃-C₆haloalkenyl, C₃-C₆alkynyl, —N(R²⁰)R¹⁹ (wherein R¹⁹ isC₁-C₆haloalkyl, —C(O)R²⁸, —C(O)OR²⁸, phenyl, phenyl substituted with(Z)_(p1), D-3, D-4, D-21, D-47, D-50, D-51, D-53 or D-54, R²⁰ ishydrogen atom or C₁-C₆alkyl, R²⁸ is C₁-C₆alkyl, C₁-C₆haloalkyl,C₃-C₆cycloalkyl C₁-C₄alkyl, C₃-C₆cycloalkyl, C₃-C₈alkenyl orC₃-C₈alkynyl), phenyl substituted with (Z)_(p1), D-8, D-10, D-13 toD-15, D-18, D-21, D-34, D-35, D-47, D-48, D-50 to D-53 and D-54.R¹-IX: C₁-C₆haloalkyl, C₁-C₆alkyl arbitrarily substituted with R¹⁶(wherein R¹⁶ is cyano, C₃-C₆cycloalkyl, C₃-C₆halocycloalkyl,C₁-C₆alkoxy, C₁-C₆haloalkoxy, C₁-C₆alkylthio, C₁-C₆haloalkylthio,C₁-C₆alkylsulfinyl, C₁-C₆haloalkylsulfinyl, C₁-C₆alkylsulfonyl,C₁-C₆haloalkylsulfonyl, C₁-C₆alkylcarbonyl, —C(O)OR²⁸, —C(O)NHR²⁹,—C(O)N(R²⁹)R²⁸, —C(S)NH₂, —C(R³¹)═NOH, —C(R³¹)═NOR³⁰, phenyl substitutedwith (Z)_(p1), D-1 to D-4, D-8 to D-38, D-47 to D-55, E-4 to E-7, E-10,E-11 or E-32, R²⁸ is C₁-C₆alkyl, C₁-C₆haloalkyl, C₃-C₆cycloalkylC₁-C₄alkyl, C₃-C₆cycloalkyl, C₃-C₈alkenyl or C₃-C₈alkynyl, R²⁹ ishydrogen atom or C₁-C₆alkyl, R³⁰ is C₁-C₆alkyl, R³¹ is hydrogen orC₁-C₆alkyl), C₃-C₆cycloalkyl, E-4, E-5, C₃-C₆alkenyl, C₃-C₆haloalkenyl,C₃-C₆alkynyl, —N(R²⁰)R¹⁹ (wherein R¹⁹ is C₁-C₆haloalkyl, —C(O)R²⁸,—C(O)OR²⁸, phenyl, phenyl substituted with (Z)_(p1), D-3, D-4, D-21,D-47, D-50, D-51, D-53 or D-54, R²⁰ is hydrogen atom or C₁-C₆alkyl, R²⁸is C₁-C₆alkyl, C₁-C₆haloalkyl, C₃-C₆cycloalkyl C₁-C₄alkyl,C₃-C₆cycloalkyl, C₃-C₈alkenyl or C₃-C₈alkynyl), phenyl substituted with(Z)_(p1), D-8, D-10, D-13 to D-15, D-18, D-21, D-34, D-35, D-47, D-48,D-50 to D-53 and D-54.R¹-X: C₁-C₈haloalkyl, C₁-C₆alkyl arbitrarily substituted with R¹⁶(wherein R¹⁶ is C₃-C₆cycloalkyl, C₁-C₆alkoxy, C₁-C₆alkylthio,C₁-C₆alkylsulfinyl, C₁-C₆alkylsulfonyl, —C(O)NH₂, —C(O)NHR²⁸, —C(S)NH₂,—C(R³¹)═NOH, —C(R³¹)═NOR³⁰, D-1 to D-4, D-8 to D-38, D-47 to D-54, E-4to E-7, E-10, E-11 or E-32, R²⁸ is C₁-C₆alkyl, C₁-C₆haloalkyl,C₃-C₆cycloalkyl, C₃-C₈alkenyl or C₃-C₈alkynyl, R³⁰ is C₁-C₆alkyl, R³¹ ishydrogen or C₁-C₆alkyl), C₃-C₆cycloalkyl, E-4, E-5, C₃-C₈alkenyl,C₃-C₈haloalkenyl, C₃-C₈alkynyl, —N(R²⁰)R¹⁹ (wherein R¹⁹ isC₁-C₆haloalkyl, —C(O)R²⁸, —C(O)OR²⁸, phenyl, D-3, D-4, D-21, D-47, D-50,D-51, D-53 or D-54, R²⁰ is hydrogen atom or C₁-C₆alkyl, R²⁸ isC₁-C₆alkyl, C₁-C₆haloalkyl, C₃-C₆cycloalkyl C₁-C₄alkyl, C₃-C₆cycloalkyl,C₃-C₈alkenyl or C₃-C₈alkynyl), D-8, D-10, D-13 to D-15, D-18, D-21,D-34, D-35, D-47, D-48, D-50 to D-53 and D-54.R¹-XI: C₁-C₆alkyl and phenyl C₁-C₆alkyl.R¹-XII: C₁-C₈alkyl, C₁-C₈alkyl arbitrarily substituted with R¹⁶ (whereinR¹⁶ is halogen atom, C₃-C₆cycloalkyl, C₃-C₆halocycloalkyl, phenyl,phenyl substituted with (Z)_(p1), D-1 to D-4, D-8 to D-42, D-47 to D-55,E-4 to E-12, E-14, E-16 to E-19, E-21 to E-23, E-26 to E-35, E-40 toE-45, E-48, M-2, M-3, M-5, M-8 to M-10, M-14, M-15 or M-16),C₃-C₈cycloalkyl and C₃-C₈halocycloalkyl.R¹-XIII: C₁-C₈alkyl arbitrarily substituted with —OR²⁵ wherein R²⁵ ishydrogen atom, C₁-C₆alkyl, C₁-C₆haloalkyl, —C(O)R³³, —C(O)OR³³,—C(O)NHR³⁴, —C(O)N(R³⁴)R³³, —C(S)NHR³⁴, —C(S)N(R³⁴)R³³, —S(O)₂R³³,—S(O)₂N(R³⁴)R³³, di(C₁-C₆alkyl)thiophosphoryl, phenyl or phenylsubstituted with (Z)_(p1), R³³ is C₁-C₆alkyl, C₁-C₆haloalkyl,C₃-C₆cycloalkyl, C₃-C₆halocycloalkyl, phenyl C₁-C₄alkyl, phenylC₁-C₄alkyl substituted with (Z)_(p1), C₃-C₆alkenyl, C₃-C₆alkynyl, phenylor phenyl substituted with (Z)_(p1), R³⁴ is hydrogen atom or C₁-C₆alkyl.R¹-XIV: C₁-C₈alkyl arbitrarily substituted with —N(R²⁶)R²⁵ wherein R²⁵is C₁-C₆alkyl, C₁-C₆haloalkyl, —C(O)R³³, —C(O)OR³³, —C(O)SR³³,—C(O)NHR³⁴, —C(O)N(R³⁴)R³³, —C(S)R³³, —C(S)OR³³, —C(S)SR³³, —C(S)NHR³⁴,—C(S)N(R³⁴)R³³, —S(O)₂R³³ or —S(O)₂N(R³⁴)R³³, R²⁶ is hydrogen atom orC₁-C₆alkyl, or R²⁶ together with R²⁵ may form 4- to 6-membered ring withthe nitrogen atom bonding them by forming C₃-C₅alkylene chain, in thiscase, the alkylene chain may contain one oxygen atom, sulfur atom ornitrogen atom, and may be substituted with C₁-C₆alkyl, oxo or thioxo,R³³ is C₁-C₆alkyl, C₁-C₆haloalkyl, C₃-C₆cycloalkyl, C₃-C₆halocycloalkyl,phenyl C₁-C₄alkyl, phenyl C₁-C₄alkyl substituted with (Z)_(p1),C₃-C₆alkenyl, C₃-C₆alkynyl, phenyl or phenyl substituted with (Z)_(p1),R³⁴ is hydrogen atom or C₁-C₆alkyl.R¹-XV: C₁-C₈alkyl arbitrarily substituted with —S(O)_(r)R²⁷ wherein R²⁷is C₁-C₆alkyl, C₁-C₆haloalkyl, tri(C₁-C₄alkyl)silyl C₁-C₄alkyl,C₁-C₆alkylthio, —C(O)NHR³⁴, —C(O)N(R³⁴)R³³, —C(S)NHR³⁴, —C(S)N(R³⁴)R³³,phenyl, phenyl substituted with (Z)_(p1), D-47 or D-50, R³³ isC₁-C₆alkyl, C₁-C₆haloalkyl, C₃-C₆cycloalkyl, C₃-C₆halocycloalkyl, phenylC₁-C₄alkyl, phenyl C₁-C₄alkyl substituted with (Z)_(p1), C₃-C₆alkenyl,C₃-C₆alkynyl, phenyl or phenyl substituted with (Z)_(p1), R³⁴ ishydrogen atom or C₁-C₆alkyl, r is an integer of 0 to 2.R¹-XVI: C₁-C₈alkyl arbitrarily substituted with R¹⁶ wherein R¹⁶ iscyano, —SO₂NHR²⁹, —SO₂N(R²⁹)R²⁸, —CHO, —C(O)R²⁸, —C(O)OR²⁸, —C(O)NHR²⁹,—C(O)N(R²⁹)R²⁸, —C(S)NHR²⁹, —C(S)N(R²⁹)R²⁸, —C(R³¹)═NOH, —C(R³¹)═NOR³⁰,—C(═NR³¹)OR³⁰, —C(═NR³¹)SR³⁰, —C(═NR³¹)N(R³⁰)R²⁹, —C(═NOR³¹)NHR²⁹ or—C(═NOR³¹)N(R³⁰)R²⁹, R²⁸ is C₁-C₆alkyl, C₁-C₆alkyl arbitrarilysubstituted with R³², C₃-C₆cycloalkyl, C₃-C₆halocycloalkyl,C₃-C₆alkenyl, C₃-C₆haloalkenyl, C₃-C₆alkynyl, C₃-C₆haloalkenyl, phenylor phenyl substituted with (Z)_(p1), R²⁹ is hydrogen atom, C₁-C₆alkyl,C₃-C₆alkenyl or C₃-C₆alkynyl, or R²⁹ together with R²⁸ may form 3- to6-membered ring with the nitrogen atom bonding them by formingC₂-C₅alkylene chain, in this case, the alkylene chain may contain oneoxygen atom or sulfur atom, R³⁰ is C₁-C₆alkyl, C₃-C₆cycloalkylC₁-C₄alkyl, phenyl C₁-C₄alkyl, phenyl C₁-C₄alkyl substituted with(Z)_(p1), C₃-C₈alkenyl or C₃-C₈alkynyl, R³¹ is hydrogen atom orC₁-C₆alkyl, or R³¹ together with R³⁰ may form 5- or 6-membered ring withthe atom bonding them by forming C₂-C₃alkylene chain, in this case, thealkylene chain may be arbitrarily substituted with C₁-C₆alkyl, R³² ishalogen atom, cyano, C₃-C₆cycloalkyl, C₃-C₆halocycloalkyl, C₁-C₄alkoxy,C₁-C₄haloalkoxy, C₁-C₄alkylthio, C₁-C₄haloalkylthio,C₁-C₄alkoxycarbonyl, —C(O)NH₂, C₁-C₄alkylaminocarbonyl,di(C₁-C₄alkyl)aminocarbonyl, phenyl or phenyl substituted with (Z)_(p1).R¹-XVII: C₃-C₈alkenyl, C₃-C₈haloalkenyl, C₃-C₈alkynyl, C₃-C₈haloalkynyl,phenyl substituted with (Z)_(p1), D-8 to D-18, D-21 to D-24, D-26 toD-40, D-42, D-45 to D-58, E-4, E-5, E-7, E-9, E-23 to E-25, E-27, E-28,E-30, E-31 and E-34.R¹-XVIII: —N(R²⁰)R¹⁹ wherein R¹⁹ is C₁-C₆alkyl, C₁-C₆haloalkyl,C₃-C₆cycloalkyl C₁-C₆alkyl, phenyl C₁-C₆alkyl, phenyl C₁-C₆alkylsubstituted with (Z)_(p1), C₃-C₆cycloalkyl, C₃-C₆alkenyl,C₃-C₆haloalkenyl, C₃-C₆alkynyl, —C(O)R²⁸, —C(O)OR²⁸, —C(O)NHR²⁹,—C(O)N(R²⁹)R²⁸, —C(S)NHR²⁹, —C(S)N(R²⁹)R²⁸, C₁-C₆alkylsulfonyl,C₁-C₆haloalkylsulfonyl, phenylsulfonyl, phenylsulfonyl substituted with(Z)_(p1), phenyl, phenyl substituted with (Z)_(p1), D-1 to D-4, D-18,D-21, D-25, D-30 to D-35, D-47 to D-55 or D-56, R²⁰ is hydrogen atom,C₁-C₆alkyl, C₁-C₄alkoxy C₁-C₄alkyl, C₁-C₄alkylthio C₁-C₄alkyl, cyanoC₁-C₆alkyl, C₃-C₆alkenyl, C₃-C₆alkynyl, —CHO, C₁-C₆alkylcarbonyl,C₁-C₆haloalkylcarbonyl, C₁-C₆alkoxycarbonyl, C₁-C₆haloalkoxycarbonyl orC₁-C₆alkylsulfonyl, R²⁸ is C₁-C₆alkyl, C₁-C₆alkyl arbitrarilysubstituted with R³², C₃-C₆cycloalkyl, C₃-C₆halocycloalkyl,C₃-C₆alkenyl, C₃-C₆haloalkenyl, C₃-C₆alkynyl, C₃-C₆haloalkynyl, phenylor phenyl substituted with (Z)_(p1), R²⁹ is hydrogen atom, C₁-C₆alkyl,C₃-C₆alkenyl or C₃-C₆alkynyl, R²⁹ together with R²⁸ may form 3- to6-membered ring with the nitrogen atom bonding them by formingC₂-C₅alkylene chain, in this case, the alkylene chain may contain oneoxygen atom or sulfur atom, R³² is hydrogen atom, cyano,C₃-C₆cycloalkyl, C₃-C₆halocycloalkyl, C₁-C₄alkoxy, C₁-C₄haloalkoxy,C₁-C₄alkylthio, C₁-C₄haloalkylthio, C₁-C₄alkoxycarbonyl, —C(O)NH₂,C₁-C₄alkylaminocarbonyl, di(C₁-C₄alkyl)aminocarbonyl, phenyl or phenylsubstituted with (Z)_(p1).

In the compounds included in the present invention, the substituent R²includes for example the following groups.

That is, R²-I: hydrogen atom.R²-II: C₁-C₆alkyl, C₁-C₆haloalkyl and C₃-C₆cycloalkyl.R²-III: C₁-C₄alkoxy C₁-C₄alkyl, C₁-C₄alkylthio C₁-C₄alkyl and cyanoC₁-C₆alkyl.R²-IV: C₃-C₆alkenyl and C₃-C₆alkynyl.R²-V: —OH, C₁-C₆alkoxy, C₁-C₆alkylcarbonyloxy, C₁-C₆alkoxycarbonyloxyand C₁-C₆alkylsulfonyloxy.R²-VI: C₁-C₆haloalkylthio, phenylthio, phenylthio substituted with(Z)_(p1) and —SN(R¹⁸)R¹⁷ wherein R¹⁷ is C₁-C₆alkyl, C₁-C₆alkoxycarbonylC₁-C₄alkyl or C₁-C₆alkoxycarbonyl, R¹⁸ is C₁-C₆alkyl or benzyl.R²-VII: —NHR²⁰ (wherein R²⁰ is hydrogen atom, C₁-C₆alkyl, —CHO,C₁-C₆alkylcarbonyl, C₁-C₆alkoxycarbonyl or C₁-C₆alkylsulfonyl),—N═CHR^(19b) and —N═C(R^(19b))R^(19a) wherein R^(19a) is C₁-C₆alkyl,R^(19b) is hydrogen atom or C₁-C₆alkyl.R²-VIII: —C(O)R⁹, —C(O)OR⁹, —C(O)SR⁹, —C(S)OR⁹, —C(S)SR⁹ (wherein R⁹ isC₁-C₆alkyl, C₁-C₆haloalkyl, C₃-C₆cycloalkyl C₁-C₄alkyl, C₁-C₆alkoxyC₁-C₄alkyl, C₁-C₆alkylthio C₁-C₄alkyl, cyano C₁-C₆alkyl, phenylC₁-C₄alkyl, C₃-C₈cycloalkyl, C₃-C₈halocycloalkyl, C₃-C₆alkenyl orC₃-C₆alkynyl) and C₁-C₆alkylsulfonyl.R²-IX: 3- to 7-membered ring that R² forms together with R¹ isaziridine, azetidine, pyrrolidine, oxazolidine, thiazoridine,piperidine, morpholine, thiomorpholine and homopiperidine.R²-X: hydrogen atom, C₁-C₆alkyl, C₁-C₄alkoxy C₁-C₄alkyl, C₁-C₄alkylthioC₁-C₄alkyl, cyano C₁-C₆alkyl, C₃-C₆cycloalkyl, C₃-C₆alkenyl,C₃-C₆alkynyl, —OH, C₁-C₆alkylcarbonyloxy, C₁-C₆alkylsulfonyloxy, —NH₂,—C(O)R⁹, —C(O)OR⁹, —C(O)SR⁹, —C(S)OR⁹ and —C(S)SR⁹ wherein R⁹ isC₁-C₆alkyl, C₁-C₆haloalkyl, C₃-C₆cycloalkyl C₁-C₄alkyl, C₁-C₆alkoxyC₁-C₄alkyl, C₁-C₆alkylthio C₁-C₄alkyl, cyano C₁-C₆alkyl,C₃-C₈cycloalkyl, C₃-C₆alkenyl or C₃-C₆alkynyl.R²-XI: hydrogen atom, C₁-C₆alkyl, C₁-C₄alkoxy C₁-C₄alkyl, cyanoC₁-C₆alkyl, C₃-C₆alkynyl, —C(O)R⁹ and —C(O)OR⁹ wherein R⁹ is C₁-C₆alkyl,C₁-C₆alkoxy C₁-C₄alkyl, C₁-C₆alkylthio C₁-C₄alkyl, C₃-C₈cycloalkyl,C₃-C₆alkenyl or C₃-C₆alkynyl.

In the compounds included in the present invention, the substituent R³includes for example the following groups.

That is, R³-I: C₁-C₆haloalkyl and C₃-C₈halocycloalkyl.R³-II: C₁-C₆alkyl, C₃-C₈cycloalkyl, E-4 to E-7, E-23 to E-27 and E-28.R³-III: C₁-C₄alkoxy C₁-C₄haloalkyl, C₁-C₄haloalkoxy C₁-C₄haloalkyl,C₁-C₄alkylthio C₁-C₄haloalkyl, C₁-C₄alkylsulfinyl C₁-C₄haloalkyl,C₁-C₄alkylsulfonyl C₁-C₄haloalkyl, C₁-C₄haloalkylthio C₁-C₄haloalkyl,C₁-C₄haloalkylsulfinyl C₁-C₄haloalkyl, C₁-C₄haloalkylsulfonylC₁-C₄haloalkyl and cyano C₁-C₆haloalkyl.R³-IV: C₃-C₆cycloalkyl C₁-C₄alkyl, C₃-C₆halocycloalkyl C₁-C₄alkyl,C₁-C₄alkoxy C₁-C₄alkyl, C₁-C₄haloalkoxy C₁-C₄alkyl, C₁-C₄alkylthioC₁-C₄alkyl, C₁-C₄alkylsulfinyl C₁-C₄alkyl, C₁-C₄alkylsulfonylC₁-C₄alkyl, C₁-C₄haloalkylthio C₁-C₄alkyl, C₁-C₄haloalkylsulfinylC₁-C₄alkyl, C₁-C₄haloalkylsulfonyl C₁-C₄alkyl and cyano C₁-C₆alkyl.R³-V: C₁-C₆haloalkyl, C₁-C₄alkoxy C₁-C₄haloalkyl, C₁-C₄haloalkoxyC₁-C₄haloalkyl, C₁-C₄alkylthio C₁-C₄haloalkyl, C₁-C₄haloalkylthioC₁-C₄haloalkyl, cyano C₁-C₆haloalkyl and C₃-C₈halocycloalkyl.R³-VI: C₁-C₆haloalkyl.R³-VII: C₁-C₆alkyl arbitrarily substituted with two or more arbitraryhalogen atoms.

Each group showing the scope of each substituent in the compoundsincluded in the present invention can be arbitrarily combined oneanother, and all combination thereof falls within the scope of thepresent invention. Examples of the combination of the scope of X, Y andR¹ include for example the combination shown in Table 1. In themeantime, the combination of Table 1 is for illustrative purposes, andthe present invention is not limited thereto.

TABLE 1 X Y R¹ X-I Y-I R¹-I X-I Y-I R¹-II X-I Y-I R¹-III X-I Y-I R¹-IVX-I Y-I R¹-V X-I Y-I R¹-VI X-I Y-I R¹-VII X-I Y-I R¹-VIII X-I Y-I R¹-IXX-I Y-I R¹-X X-I Y-I R¹-XI X-I Y-II R¹-I X-I Y-II R¹-II X-I Y-II R¹-IIIX-I Y-II R¹-IV X-I Y-II R¹-V X-I Y-II R¹-VI X-I Y-II R¹-VII X-I Y-IIR¹-VIII X-I Y-II R¹-IX X-I Y-II R¹-X X-I Y-II R¹-XI X-I Y-III R¹-I X-IY-III R¹-VII X-I Y-III R¹-VIII X-I Y-III R¹-IX X-I Y-III R¹-X X-I Y-IVR¹-I X-I Y-IV R¹-II X-I Y-IV R¹-III X-I Y-IV R¹-IV X-I Y-IV R¹-V X-IY-IV R¹-VI X-I Y-IV R¹-VII X-I Y-IV R¹-VIII X-I Y-IV R¹-IX X-I Y-IV R¹-XX-I Y-IV R¹-XI X-I Y-V R¹-I X-I Y-V R¹-II X-I Y-V R¹-III X-I Y-V R¹-IVX-I Y-V R¹-V X-I Y-V R¹-VI X-I Y-V R¹-VII X-I Y-V R¹-VIII X-I Y-V R¹-IXX-I Y-V R¹-X X-I Y-V R¹-XI X-I Y-VI R¹-I X-I Y-VI R¹-II X-I Y-VI R¹-IIIX-I Y-VI R¹-IV X-I Y-VI R¹-V X-I Y-VI R¹-VI X-I Y-VI R¹-VII X-I Y-VIR¹-VIII X-I Y-VI R¹-IX X-I Y-VI R¹-X X-I Y-VI R¹-XI X-II Y-I R¹-I X-IIY-I R¹-II X-II Y-I R¹-III X-II Y-I R¹-IV X-II Y-I R¹-V X-II Y-I R¹-VIX-II Y-I R¹-VII X-II Y-I R¹-VIII X-II Y-I R¹-IX X-II Y-I R¹-X X-II Y-IIR¹-X X-II Y-III R¹-X X-II Y-IV R¹-X X-II Y-V R¹-X X-II Y-VI R¹-I X-IIY-VI R¹-II X-II Y-VI R¹-III X-II Y-VI R¹-IV X-II Y-VI R¹-V X-II Y-VIR¹-VI X-II Y-VI R¹-VII X-II Y-VI R¹-VIII X-II Y-VI R¹-IX X-II Y-VI R¹-XX-III Y-I R¹-I X-III Y-I R¹-II X-III Y-I R¹-III X-III Y-I R¹-IV X-IIIY-I R¹-V X-III Y-I R¹-VI X-III Y-I R¹-VII X-III Y-I R¹-VIII X-III Y-IR¹-IX X-III Y-I R¹-X X-III Y-I R¹-XI X-III Y-II R¹-X X-III Y-III R¹-XX-III Y-IV R¹-X X-III Y-V R¹-X X-III Y-VI R¹-I X-I Y-I R¹-XII X-I Y-IR¹-XIII X-I Y-I R¹-XIV X-I Y-I R¹-XV X-I Y-I R¹-XVI X-I Y-I R¹-XVII X-IY-I R¹-XVIII X-III Y-I R¹-XII X-III Y-I R¹-XIII X-III Y-I R¹-XIV X-IIIY-I R¹-XV X-III Y-I R¹-XVI X-III Y-I R¹-XVII X-III Y-I R¹-XVIII X-IIIY-VI R¹-II X-III Y-VI R¹-III X-III Y-VI R¹-IV X-III Y-VI R¹-V X-III Y-VIR¹-VI X-III Y-VI R¹-VII X-III Y-VI R¹-VIII X-III Y-VI R¹-IX X-III Y-VIR¹-X X-III Y-VI R¹-XI X-IV Y-I R¹-I X-IV Y-I R¹-II X-IV Y-I R¹-III X-IVY-I R¹-IV X-IV Y-I R¹-V X-IV Y-I R¹-VI X-IV Y-I R¹-VII X-IV Y-I R¹-VIIIX-IV Y-I R¹-IX X-IV Y-I R¹-X X-IV Y-I R¹-XI X-IV Y-II R¹-X X-IV Y-IIIR¹-X X-IV Y-IV R¹-X X-IV Y-V R¹-X X-IV Y-VI R¹-I X-IV Y-VI R¹-II X-IVY-VI R¹-III X-IV Y-VI R¹-IV X-IV Y-VI R¹-V X-IV Y-VI R¹-VI X-IV Y-VIR¹-VII X-IV Y-VI R¹-VIII X-IV Y-VI R¹-IX X-IV Y-VI R¹-X X-IV Y-VI R¹-XIX-V Y-I R¹-I X-V Y-I R¹-VII X-V Y-I R¹-IX X-V Y-I R¹-X X-V Y-II R¹-X X-VY-III R¹-X X-V Y-IV R¹-X X-V Y-V R¹-X X-V Y-VI R¹-I X-V Y-VI R¹-VII X-VY-VI R¹-IX X-V Y-VI R¹-X X-VI Y-I R¹-I X-VI Y-I R¹-II X-VI Y-I R¹-IIIX-VI Y-I R¹-IV X-VI Y-I R¹-V X-VI Y-I R¹-VI X-VI Y-I R¹-VII X-VI Y-IR¹-VIII X-VI Y-I R¹-IX X-VI Y-I R¹-X X-VI Y-II R¹-X X-VI Y-III R¹-X X-VIY-IV R¹-X X-VI Y-V R¹-X X-VI Y-VI R¹-I X-VI Y-VI R¹-II X-VI Y-VI R¹-IIIX-VI Y-VI R¹-IV X-VI Y-VI R¹-V X-VI Y-VI R¹-VI X-VI Y-VI R¹-VII X-VIY-VI R¹-VIII X-VI Y-VI R¹-IX X-VI Y-VI R¹-X X-VII Y-I R¹-I X-VII Y-IR¹-II X-VII Y-I R¹-III X-VII Y-I R¹-IV X-VII Y-I R¹-V X-VII Y-I R¹-VIX-VII Y-I R¹-VII X-VII Y-I R¹-VIII X-VII Y-I R¹-IX X-VII Y-I R¹-X X-VIIY-II R¹-X X-VII Y-III R¹-X X-VII Y-IV R¹-X X-VII Y-V R¹-X X-VII Y-VIR¹-I X-VII Y-VI R¹-II X-VII Y-VI R¹-III X-VII Y-VI R¹-IV X-VII Y-VI R¹-VX-VII Y-VI R¹-VI X-VII Y-VI R¹-VII X-VII Y-VI R¹-VIII X-VII Y-VI R¹-IXX-VII Y-VI R¹-X X-VIII Y-I R¹-X X-VIII Y-VI R¹-X X-IX Y-I R¹-X X-IX Y-VIR¹-X X-I Y-VI R¹-XII X-I Y-VI R¹-XIII X-I Y-VI R¹-XIV X-I Y-VI R¹-XV X-IY-VI R¹-XVI X-I Y-VI R¹-XVII X-I Y-VI R¹-XVIII X-III Y-VI R¹-XII X-IIIY-VI R¹-XIII X-III Y-VI R¹-XIV X-III Y-VI R¹-XV X-III Y-VI R¹-XVI X-IIIY-VI R¹-XVII X-III Y-VI R¹-XVIII

The compounds of the present invention can be produced for exampleaccording to the methods mentioned below.

Production Method A

The compound of formula (1-1) wherein A¹, A², A³, G, X, Y, R¹, R², R³, mand n are as defined above that is the compound of formula (1) wherein Wis oxygen atom can be obtained by reacting the compound of formula (5)wherein A¹, A², A³, G, X, Y, R³, m and n are as defined above with thecompound of formula (6) wherein R¹ and R² are as defined above by use ofa condensation agent, optionally by using a solvent inactive for thereaction, optionally in the presence of a base.

The reaction substrates can be used in an amount of 1 to 100 equivalentsof the compound of formula (6) based on 1 equivalent of the compound offormula (5).

The condensation agent is not specifically limited if it is a compoundused for ordinary amide synthesis, but it is for example Mukaiyama agent(2-chloro-N-methylpyridinium iodide), DCC (1,3-dicyclohexylcarbodiimide), WSC (1-ethyl-3-(3-dimethylaminopropyl)-carbodiimidehydrochloride), CDI (carbonyl diimidazole), dimethylpropynyl sulfoniumbromide, propagyl triphenyl phosphonium bromide, DEPC (diethylphosphorocyanidate) or the like, and can be used in an amount of 1 to 4equivalents based on the compound of formula (5).

In case where a solvent is used, the solvent is not specifically limitedif it dose not inhibit the progress of the reaction, but it includes forexample aromatic hydrocarbons such as benzene, toluene, xylene or thelike, aliphatic hydrocarbons such as hexane, heptane or the like,alicyclic hydrocarbons such as cyclohexane or the like, aromatichalogenated hydrocarbons such as chlorobenzene, dichlorobenzene or thelike, aliphatic halogenated hydrocarbons such as dichloro methane,chloroform, carbon tetrachloride, 1,2-dichloroethane,1,1,1-trichloroethane, trichloroethylene, tetrachloroethylene or thelike, ethers such as diethyl ether, 1,2-dimethoxyethane,tetrahydrofuran, 1,4-dioxane or the like, esters such as ethyl acetate,ethyl propionate or the like, amides such as N,N-dimethylformamide,N,N-dimethylacetamide, N-methyl-2-pyrolidone or the like, amines such astriethyl amine, tributyl amine, N,N-dimethyl aniline or the like,pyridines such as pyridine, picoline or the like, acetonitrile anddimethyl sulfoxide, and the like. These solvents may be used alone or ina mixture of two or more.

The addition of a base is not necessarily required. However, when thebase is used, alkali metal hydroxides such as sodium hydroxide,potassium hydroxide or the like, alkali metal carbonates such as sodiumcarbonate, potassium carbonate or the like, alkali metal bicarbonatessuch as sodium hydrogen carbonate, potassium hydrogen carbonate or thelike, organic bases such as triethylamine, tributylamine,N,N-dimethylaniline, pyridine, 4-(dimethylamino)pyridine, imidazole,1,8-diazabicyclo[5.4.0]-7-undecene, and the like can be used in anamount of 1 to 4 equivalents based on the compound of formula (5).

The reaction temperature may be an arbitrary temperature ranging from−60° C. to the reflux temperature of a reaction mixture, and thereaction time may be an arbitrary time ranging from 5 minutes to 100hours although it varies depending on the concentration of the reactionsubstrates or the reaction temperature.

Generally, it is preferable to carry out the reaction by using 1 to 20equivalents of the compound of formula (6) and 1 to 4 equivalent of thecondensation agent such as WSC(1-ethyl-3-(3-dimethylaminopropyl)-carbodiimide hydrochloride), CDI(carbonyl diimidazole) or the like based on 1 equivalent of the compoundof formula (5), optionally in the presence of 1 to 4 equivalents of abase such as potassium carbonate, triethylamine, pyridine,4-(dimethylamino)pyridine or the like, without solvent or in a solventsuch as dichloromethane, chloroform, diethyl ether, tetrahydrofurane,1,4-dioxane or the like, at a temperature ranging from 0° C. to thereflux temperature of these solvents for 10 minutes to 24 hours.

In addition, the compound of formula (1-1) according to the presentinvention can be also synthesized by reacting the compound of formula(7) wherein A¹, A², A³, G, X, Y, R³, m and n are as defined above, J′ ischlorine atom, bromine atom, C₁-C₄alkylcarbonyloxy (for examplepivaloyloxy), C₁-C₄alkoxycarbonyloxy (for exampleisobutyloxycarbonyloxy) or azolyl (for example imidazol-1-yl) that canbe synthesized according to a known method disclosed in documents fromthe compound of formula (5), for example a method by reacting with achlorinating agent such as thionyl chloride, phosphorus pentachloride oroxalyl chloride, a method by reacting with a organic acid halide such aspivaloyl chloride or isobutyl chlorformate, etc. optionally in thepresence of a base, or a method by reacting with carbonyl diimidazole orsulfonyl diimidazole, etc., with the compound of formula (6), optionallyby using a solvent inactive for the reaction, optionally in the presenceof a base.

The reaction substrates can be used in an amount of 1 to 50 equivalentsof the compound of formula (6) based on 1 equivalent of the compound offormula (7).

In case where a solvent is used, the solvent is not specifically limitedif it dose not inhibit the progress of the reaction, but it includes forexample aromatic hydrocarbons such as benzene, toluene, xylene or thelike, aliphatic hydrocarbons such as hexane, heptane or the like,alicyclic hydrocarbons such as cyclohexane or the like, aromatichalogenated hydrocarbons such as chlorobenzene, dichlorobenzene or thelike, aliphatic halogenated hydrocarbons such as dichloro methane,chloroform, carbon tetrachloride, 1,2-dichloroethane,1,1,1-trichloroethane, trichloroethylene, tetrachloroethylene or thelike, ethers such as diethyl ether, 1,2-dimethoxyethane,tetrahydrofuran, 1,4-dioxane or the like, esters such as ethyl acetate,ethyl propionate or the like, amides such as N,N-dimethylformamide,N,N-dimethylacetamide, N-methyl-2-pyrolidone or the like, amines such astriethyl amine, tributyl amine, N,N-dimethyl aniline or the like,pyridines such as pyridine, picoline or the like, acetonitrile andwater, and the like. These solvents may be used alone or in a mixture oftwo or more.

The addition of a base is not necessarily required. However, when thebase is used, alkali metal hydroxides such as sodium hydroxide,potassium hydroxide or the like, alkali metal carbonates such as sodiumcarbonate, potassium carbonate or the like, alkali metal bicarbonatessuch as sodium hydrogen carbonate, potassium hydrogen carbonate or thelike, organic bases such as triethylamine, tributylamine,N,N-dimethylaniline, pyridine, 4-(dimethylamino)pyridine, imidazole,1,8-diazabicyclo[5.4.0]-7-undecene, and the like can be used in anamount of 1 to 4 equivalents based on the compound of formula (7).

The reaction temperature may be an arbitrary temperature ranging from−60° C. to the reflux temperature of a reaction mixture, and thereaction time may be an arbitrary time ranging from 5 minutes to 100hours although it varies depending on the concentration of the reactionsubstrates or the reaction temperature.

Generally, it is preferable to carry out the reaction by using 1 to 10equivalents of the compound of formula (6) based on 1 equivalent of thecompound of formula (7), optionally in the presence of 1 to 2equivalents of a base such as potassium carbonate, triethylamine,pyridine, 4-(dimethylamino)pyridine or the like, without solvent or in asolvent such as dichloromethane, chloroform, diethyl ether,tetrahydrofurane, 1,4-dioxane, ethyl acetate, acetonitrile or the like,at a temperature ranging from 0° C. to the reflux temperature of thesesolvents for 10 minutes to 24 hours.

Production Method B

Hydroxamic chloride of formula (9) wherein A¹, A², A³, W, Y, R¹, R² andn are as defined above, J² means halogen atom such as chlorine atom andbromine atom can be obtained by halogenating the compound of formula (8)wherein A¹, A², A³, W, Y, R¹, R² and n are as defined above using ahalogenating reagent optionally by using a solvent inactive for thereaction, optionally in the presence of a base.

Halogenating agents include for example N-halosuccinimides such asN-chlorosuccinimide, N-bromosuccinimide or the like, hypohalogenous acidalkali metal salts such as sodium hypochlorite or the like,hypohalogenous acid esters such as hypochlorous acid-t-butyl ester orthe like, simple substance halogens such as chlorine gas or the like,and it can be used in an amount of 1 to 10 equivalents based on thecompound of formula (8).

In case where a solvent is used, the solvent is not specifically limitedif it dose not inhibit the progress of the reaction, but it includes forexample aromatic hydrocarbons such as benzene, toluene, xylene or thelike, aliphatic hydrocarbons such as hexane, heptane or the like,alicyclic hydrocarbons such as cyclohexane or the like, aromatichalogenated hydrocarbons such as chlorobenzene, dichlorobenzene or thelike, aliphatic halogenated hydrocarbons such as dichloro methane,chloroform, carbon tetrachloride, 1,2-dichloroethane,1,1,1-trichloroethane, trichloroethylene, tetrachloroethylene or thelike, ethers such as diethyl ether, 1,2-dimethoxyethane,tetrahydrofuran, 1,4-dioxane or the like, esters such as ethyl acetate,ethyl propionate or the like, amides such as N,N-dimethylformamide,N,N-dimethylacetamide, N-methyl-2-pyrolidone or the like, alcohols suchas methanol, ethanol, ethylene glycol or the like, carboxylic acids suchas acetic acid, propionic acid or the like, acetonitrile and water, andthe like. These solvents may be used alone or in a mixture of two ormore.

The reaction temperature may be an arbitrary temperature ranging from−60° C. to the reflux temperature of a reaction mixture, and thereaction time may be an arbitrary time ranging from 5 minutes to 24hours although it varies depending on the concentration of the reactionsubstrates or the reaction temperature.

The compounds of formula (1) wherein A¹, A², A³, G, W, X, Y, R¹, R², R³,m and n are as defined above according to the present invention can beobtained by reacting the compound of formula (9) with the compound offormula (10) wherein G, X, R³ and m are as defined above in the presenceof a base optionally by use of a solvent inactive for the reaction.

The reaction substrates can be used in an amount of 1 to 5 equivalentsof the compound of formula (10) based on 1 equivalent of the compound offormula (9).

The used base includes for example alkali metal hydroxides such assodium hydroxide, potassium hydroxide or the like, alkali metalcarbonates such as sodium carbonate, potassium carbonate or the like,alkali metal bicarbonates such as sodium hydrogen carbonate, potassiumhydrogen carbonate or the like, organic bases such as triethylamine,tributylamine, N,N-dimethylaniline, pyridine, 4-(dimethylamino)pyridine,imidazole, 1,8-diazabicyclo[5.4.0]-7-undecene, and the like can be usedin an amount of 1 to 5 equivalents based on the compound of formula (9).

In case where a solvent is used, the solvent is not specifically limitedif it dose not inhibit the progress of the reaction, but it includes forexample aromatic hydrocarbons such as benzene, toluene, xylene or thelike, aliphatic hydrocarbons such as hexane, heptane or the like,alicyclic hydrocarbons such as cyclohexane or the like, aromatichalogenated hydrocarbons such as chlorobenzene, dichlorobenzene or thelike, aliphatic halogenated hydrocarbons such as dichloro methane,chloroform, carbon tetrachloride, 1,2-dichloroethane,1,1,1-trichloroethane, trichloroethylene, tetrachloroethylene or thelike, ethers such as diethyl ether, 1,2-dimethoxyethane,tetrahydrofuran, 1,4-dioxane or the like, esters such as ethyl acetate,ethyl propionate or the like, amides such as N,N-dimethylformamide,N,N-dimethylacetamide, N-methyl-2-pyrolidone or the like, andacetonitrile, and the like. These solvents may be used alone or in amixture of two or more.

The reaction temperature may be an arbitrary temperature ranging from−60° C. to the reflux temperature of a reaction mixture, and thereaction time may be an arbitrary time ranging from 5 minutes to 100hours although it varies depending on the concentration of the reactionsubstrates or the reaction temperature.

Generally, the compound of formula (9) can be obtained for example bycarrying out the reaction by using 1 to 2 equivalents of a halogenatingagent such as N-chlorosuccinimide, sodium hypochlorite aqueous solution,hypochlorous acid-t-butyl ester, chlorine gas or the like based on 1equivalent of the compound of formula (8) in a solvent such asdichloromethane, chloroform, 1,2-dimethoxyethane, tetrahydrofurane,1,4-dioxane, N,N-dimethylformamide or the like, at a temperature rangingfrom 0° C. to the reflux temperature of these solvents for 10 minutes to2 hours. Then, preferably without the isolation of the compound offormula (9), 1 to 2 equivalents of the compound of formula (10) and 1 to2 equivalents of a base such as sodium carbonate, sodium hydrogencarbonate, triethyl amine or the like are added, and the reaction iscarried out at a temperature ranging from 0° C. to the refluxtemperature of these solvents for 10 minutes to 24 hours.

Production Method C

The compound of formula (1-1) wherein A¹, A², A³, G, X, Y, R¹, R³, m andn are as defined above and R² has the same meaning defined aboveexcluding hydrogen atom according to the present invention that is thecompound of formula (1) wherein W is oxygen atom can be obtained byreacting the compound of formula (1-2) wherein A¹, A², A³, G, X, Y, R¹,R³, m and n are as defined above that is the compound of formula (1)wherein W is oxygen atom and R² is hydrogen atom with the compound offormula (11) wherein R² has the same meaning defined above excludinghydrogen atom, J³ is a good leaving group such as chlorine atom, bromineatom, iodine atom, C₁-C₄alkylcarbonyloxy (for example pivaloyloxy),C₁-C₄alkylsulfonate (for example methane sulfonyloxy),C₁-C₄haloalkylsulfonate (for example trifluoromethane sulfonyloxy),arylsulfonate (for example benzene sulfonyloxy, p-toluene sulfonyloxy)or azolyl (for example imidazol-1-yl), optionally in the presence of abase, optionally by using a solvent inactive for the reaction.

The reaction substrates can be used in an amount of 1 to 50 equivalentsof the compound of formula (11) based on 1 equivalent of the compound offormula (1-2).

In case where a solvent is used, the solvent is not specifically limitedif it dose not inhibit the progress of the reaction, but it includes forexample aromatic hydrocarbons such as benzene, toluene, xylene or thelike, aliphatic hydrocarbons such as hexane, heptane or the like,alicyclic hydrocarbons such as cyclohexane or the like, aromatichalogenated hydrocarbons such as chlorobenzene, dichlorobenzene or thelike, aliphatic halogenated hydrocarbons such as dichloro methane,chloroform, carbon tetrachloride, 1,2-dichloroethane,1,1,1-trichloroethane, trichloroethylene, tetrachloroethylene or thelike, ethers such as diethyl ether, 1,2-dimethoxyethane,tetrahydrofuran, 1,4-dioxane or the like, esters such as ethyl acetate,ethyl propionate or the like, amides such as N,N-dimethylformamide,N,N-dimethylacetamide, N-methyl-2-pyrolidone or the like, amines such astriethyl amine, tributyl amine, N,N-dimethyl aniline or the like,pyridines such as pyridine, picoline or the like, alcohols such asmethanol, ethanol, ethylene glycol or the like, acetonitrile,dimethylsulfoxide, sulfolane, 1,3-dimethyl-2-imidazolidinone and water,and the like. These solvents may be used alone or in a mixture of two ormore.

When the base is used, alkali metal hydride such as sodium hydride,potassium hydride or the like, alkali metal hydroxides such as sodiumhydroxide, potassium hydroxide or the like, alkali metal alkoxides suchas sodium ethoxide, potassium t-butoxide or the like, alkali metalamides such as lithium diisopropylamide, lithium hexamethyl disilazane,sodium amide or the like, organic metal compounds such as t-butyllithium or the like, alkali metal carbonates such as sodium carbonate,potassium carbonate, sodium hydrogen carbonate or the like, organicbases such as triethylamine, tributylamine, N,N-dimethylaniline,pyridine, 4-(dimethylamino)pyridine, imidazole,1,8-diazabicyclo[5.4.0]-7-undecene, and the like can be used in anamount of 1 to 4 equivalents based on the compound of formula (1-2).

The reaction temperature may be an arbitrary temperature ranging from−60° C. to the reflux temperature of a reaction mixture, and thereaction time may be an arbitrary time ranging from 5 minutes to 100hours although it varies depending on the concentration of the reactionsubstrates or the reaction temperature.

Generally, it is preferable to carry out the reaction by using 1 to 10equivalents of the compound of formula (11) based on 1 equivalent of thecompound of formula (1-2), in a polar solvent such as tetrahydrofurane,1,4-dioxane, acetonitrile, N,N-dimethylformamide or the like, optionallyin the presence of 1 to 3 equivalents of a base such as sodium hydride,potassium t-butoxide, potassium hydroxide, potassium carbonate,triethylamine, pyridine or the like, based on 1 equivalent of thecompound of formula (1-2), at a temperature ranging from 0 to 90° C. for10 minutes to 24 hours.

Production Method D

The compound of formula (1-3) wherein A¹, A², A³, G, X, Y, R¹, R², R³, mand n are as defined above according to the present invention that isthe compound of formula (1) wherein W is sulfur atom can be obtained byreacting the compound of formula (1-1) wherein A¹, A², A³, G, X, Y, R¹,R², R³, m and n are as defined above according to the present inventionthat is the compound of formula (1) wherein W is oxygen atom with asulfurizing agent such as diphosphorus pentasulfide, diphosphoruspentasulfide-HMDO (hexamethyldisiloxane), Lawesson's Reagent(2,4-bis(4-methoxyphenyl)-1,3,2,4-dithiadiphosphetane-2,4-disulfide),optionally by using a solvent inactive for the reaction, optionally inthe presence of a base.

The reaction substrates can be used in an amount of 1 to 50 equivalentsof the sulfurizing agent based on 1 equivalent of the compound offormula (1-1).

In case where a solvent is used, the solvent is not specifically limitedif it dose not inhibit the progress of the reaction, but it includes forexample aromatic hydrocarbons such as benzene, toluene, xylene or thelike, aliphatic hydrocarbons such as hexane, heptane or the like,alicyclic hydrocarbons such as cyclohexane or the like, aromatichalogenated hydrocarbons such as chlorobenzene, dichlorobenzene or thelike, aliphatic halogenated hydrocarbons such as dichloro methane,chloroform, carbon tetrachloride, 1,2-dichloroethane,1,1,1-trichloroethane, trichloroethylene, tetrachloroethylene or thelike, ethers such as diethyl ether, 1,2-dimethoxyethane,tetrahydrofuran, 1,4-dioxane or the like, amines such as triethyl amine,tributyl amine, N,N-dimethyl aniline or the like, pyridines such aspyridine, picoline or the like, and HMPA (hexamethylphosphorictriamide), and the like. These solvents may be used alone or in amixture of two or more.

The addition of a base is not necessarily required. However, when thebase is used, alkali metal carbonates such as sodium carbonate,potassium carbonate, sodium hydrogen carbonate or the like, organicbases such as triethylamine, tributylamine, N,N-dimethylaniline,pyridine, 4-(dimethylamino)pyridine, imidazole,1,8-diazabicyclo[5.4.0]-7-undecene, and the like can be used in anamount of 1 to 10 equivalents based on the compound of formula (1-1).

The reaction temperature may be an arbitrary temperature ranging from 0°C. to the reflux temperature of a reaction mixture, and the reactiontime may be an arbitrary time ranging from 5 minutes to 100 hoursalthough it varies depending on the concentration of the reactionsubstrates or the reaction temperature.

Generally, it is preferable to carry out the reaction by using 1 to 10equivalents of a sulfurizing agent such as diphosphorus pentasulfide,diphosphorus pentasulfide-HMDO, Lawesson's Reagent or the like, based on1 equivalent of the compound of formula (1-1), optionally in thepresence of 1 to 4 equivalents of a base such as sodium hydrogencarbonate, triethylamine, pyridine or the like, in a solvent such asbenzene, toluene, chlorobenzene, dichloromethane, chloroform,1,2-dimethoxyethane, tetrahydrofurane, 1,4-dioxane, HMPA or the like, ata temperature ranging from room temperature to the reflux temperature ofthe reaction mixture for 10 minutes to 50 hours, or in a solvent amountof pyridine at a temperature of 80° C. to the reflux temperature of thereaction mixture for 1 to 3 hours.

In Production Method A to Production Method D, the aimed compound of thepresent invention can be obtained by subjecting the reaction mixtureafter the completion of the reaction to ordinary post-treatment such asa direct concentration, or a concentration after dissolving in anorganic solvent and washing with water or a concentration after placingin ice water and extracting with an organic solvent. In addition, when apurification is required, it can be separated and purified by anarbitrary purification process such as recrystallization, columnchromatograph, thin layer chromatograph, liquid chromatograph collectionor the like.

The compound of formula (5) used in Production Method A can besynthesized as follows, for example.

That is, the compound of formula (5) wherein A¹, A², A³, G, X, Y, R³, mand n are as defined above can be obtained by reacting the compound offormula (12) wherein A¹, A², A³, G, X, Y, R³, m and n are as definedabove, J⁴ is bromine atom, iodine atom, halosulfonyloxy (for examplefluorosulfonyloxy), C₁-C₄haloalkylsulfonyloxy (for exampletrifluoromethane sulfonyloxy) or arylsulfonyloxy (for examplebenzenesulfonyloxy) according to a known method disclosed in documents,for example by CO insertion reaction by use of a transition metalcatalyst such as palladium or the like stated in J. Org. Chem., 1999,vol. 64, p. 6921 or the like, or by a process by lithiation and thenreaction with carbonic acid gas stated in Chem. Rev., 1990, vol. 90, p.879.

In addition, the compound of formula (5) can be obtained by subjectingthe compound of formula (12) to a reaction according to a reactioncondition for CO insertion reaction by use of a transition metalcatalyst such as palladium or the like stated in J. Org. Chem., 1974,vol. 39, p. 3318 or the like to convert the compound of formula (13)wherein A¹, A², A³, G, X, Y, R³, m and n are as defined above, R^(b) isC₁-C₆alkyl such as methyl, ethyl or the like, and then hydrolizingaccording to an ordinary ester hydrolysis disclosed in documents, forexample a reaction condition stated in Angew. Chem., 1951, vol. 63, p.329, J. Am. Chem. Soc., 1929, vol. 51, p. 1865 or the like.

Some of the compounds of formula (6) used in Production Method A areknown compounds, and a part thereof is commercially available. Also, thecompounds other than the above-mentioned compounds can be synthesizedaccording to methods stated in for example Justus Liebigs Ann. Chem.,1979, p. 920, U.S. Pat. No. 5,990,323, WO 96/11200 or the like, andgeneral synthetic methods for primary or secondary alkyl aminesdisclosed in documents.

The compounds of formula (8) used in Production Method B can besynthesized as follows, for example.

That is, the compound of formula (8) wherein A¹, A², A³, W, Y, R¹, R²and n are as defined above can be easily synthesized by reacting thecompound of formula (14) wherein A¹, A², A³, W, Y, R¹, R² and n are asdefined above with hydroxyamine or the salt thereof according to knownmethods disclosed in documents, for example the method stated in J. Med.Chem., 2001, vol. 44, p. 2308 or the like.

The compounds of formula (10) used in Production Method B can besynthesized as follows, for example.

That is, the compound of formula (10) wherein G, X, R³ and m are asdefined above can be obtained by reacting the known compound of formula(15) wherein G, X and m are as defined above, J⁵ is bromine atom, iodineatom, C₁-C₄haloalkylsulfonyloxy (for exampletrifluoromethanesulfonyloxy), —B(OH)₂,4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl, —Si(OEt)₃, —ZnCl, —ZnBr or—Znl, etc. with the compound of formula (16) wherein R³ is as definedabove, J⁶ is halogen atom such as bromine atom, iodine atom or the like,or —B(OH)₂ according to an ordinary crosscoupling reaction by use of atransition metal catalyst such as palladium or the like disclosed indocuments, for example a reaction condition stated in J. Org. Chem.,1991, vol. 56, p. 7336, Tetrahedron Lett., 2001, vol. 42, p. 4083, orthe like.

Some of the compounds of formula (16) used in the above-mentionedprocess are known compounds, and a part thereof is commerciallyavailable. Also, the compounds other than the above-mentioned compoundscan be synthesized according to methods disclosed in documents, forexample a method stated in J. Am. Chem. Soc., 1971, vol. 93, p. 1925,Tetrahedron Lett., 1990, vol. 31, p. 1919 and 2001, vol. 42, p. 4083 orthe like.

In addition, the compounds of formula (10) can be obtained by reactingthe compound of formula (17) wherein G, X, R³ and m are as defined aboveaccording to a reaction of converting carbonyl to olefine disclosed indocuments, for example a reaction condition stated in J. Org. Chem.,1986, vol. 51, p. 5252 and 1994, vol. 59, p. 2898, Synthesis, 1991, p.29, Tetrahedron Lett., 1985, vol. 26, p. 5579 or the like.

Some of the compounds of formula (11) used in Production method C areknown compounds, and a part thereof is commercially available. Also, thecompounds other than the above-mentioned compounds can be easilysynthesized according to methods disclosed in documents, for example amethod stated in Chem. Lett., 1976, p. 373, J. Am. Chem. Soc., 1964,vol. 86, p. 4383, J. Org. Chem., 1976, vol. 41, p. 4028 and 1978, vol.43, p. 3244, Org. Synth., 1988, Corrective vol. 6, p. 101, TetrahedronLett., 1972, p. 4339, GB 2,161,802, EP 0,051,273 or the like.

The compounds of formula (12) can be synthesized as follows, forexample.

That is, the compounds of formula (12) wherein A¹, A², A³, G, X, Y, R³,m, n and J⁴ are as defined above can be obtained by halogenating thecompound of formula (18) wherein A¹, A², A³, Y, n and J⁴ are as definedabove under a condition similar to that of Production Method B to obtainthe compound of formula (19) wherein A¹, A², A³, Y, n, J³ and J⁴ are asdefined above, and then reacting it with the compound of formula (10)wherein G, X, R³ and m are as defined above.

The compound of formula (18) can be easily synthesized by use of thecorresponding known substituted aromatic aldehyde similarly to theprocess described in Reaction Scheme 2.

The compound of formula (14) can be synthesized for example according toReaction Scheme 5 or Reaction Scheme 6.

The compounds of formula (14) wherein A¹, A², A³, W, Y, R¹, R² and n areas defined above can be obtained by subjecting the compound of formula(20) wherein A¹, A², A³, W, Y, R¹, R², n and J⁴ are as defined above toCO insertion reaction according to known methods disclosed in documents,for example the reaction by use of a transition metal catalyst such aspalladium or the like in the presence of hydride source such as formicacid or the like stated in Bull. Chem. Soc. Jpn., 1994, vol. 67, p.2329, J. Am. Chem. Soc., 1986, vol. 108, p. 452, or the like.

The compounds of formula (14-1) wherein A¹, A², A³, Y, R¹, R² and n areas defined above that are the compounds of formula (14) wherein W isoxygen atom can be synthesized by reacting the known compound of formula(21) wherein A¹, A², A³, Y and n are as defined above with the compoundof formula (6) wherein R¹ and R² are as defined above by use of themethod similar to Production Method A.

The compounds of formula (17) can be synthesized as follows, forexample.

That is, the compounds of formula (17) wherein X, R³ and m are asdefined above, G is benzene ring can be obtained by reacting the knowncompound of formula (23) wherein X and m are as defined above, G isbenzene ring with the known compound of formula (24) wherein R³ is asdefined above, J⁷ is a leaving group such as halogen atom,trifluoromethanesulfonyloxy, 2-pyridyloxy or the like, or the knowncompound of formula (25) wherein R³ is as defined above according to ageneral acylating reaction of aromatic ring disclosed in documents, forexample a method stated in Chem. Lett., 1990, p. 783, J. Org. Chem.,1991, vol. 56, p. 1963 or the like.

In addition, the compound of formula (17) wherein G, X, R³ and m are asdefined above can be obtained according to general methods disclosed indocuments for example by a method stated in J. Am. Chem. Soc., 1955,vol. 77, p. 3657, Tetrahedron Lett., 1980, vol. 21, p. 2129 and 1991,vol. 32, p. 2003, U.S. Pat. No. 5,514,816 in which the compound offormula (26) wherein G, X and m are as defined above, J⁸ is bromine atomor iodine atom is lithiated and the resulting compound is reacted withthe known compound of formula (27) wherein R³ is as defined above, J⁹ ishalogen atom, hydroxy, metal salt (for example, —OLi, —ONa), C₁-C₄alkoxy(for example, methoxy, ethoxy), di(C₁-C₄alkyl)amino (for example,diethylamino), C₁-C₄alkoxy C₁-C₄alkyl amino(for exampleO,N-dimethylhydroxyamino) or cyclic amino (for example, piperidin-1-yl,morpholin-4-yl, 4-methylpiperadin-1-yl), or the known compound offormula (25), or by a method stated in Heterocycles, 1987, vol. 25, p.221, Synth. Commun., 1985, vol. 15, p. 1291 and 1990, vol. 20, p. 1469,DE 19727042, or the like in which a Grignard reagent is formed and thenit is reacted with the compound of formula (27) or the compound offormula (25).

The compounds of formula (20) can be synthesized according to forexample Reaction Scheme 8 or Reaction Scheme 9.

The compounds of formula (20-1) wherein A¹, A², A³, Y, R¹, R², n and J⁴are as defined above that are the compounds of formula (20) wherein W isoxygen atom can be obtained by reacting the known compound of formula(28) wherein A¹, A², A³, Y, n and J⁴ are as defined above with thecompound of formula (6) wherein R¹ and R² are as defined above by use ofthe method similar to Production Method A.

The compounds of formula (20-2) wherein A¹, A², A³, Y, R¹, R², n and J⁵are as defined above that are the compounds of formula (20) wherein W issulfur atom can be obtained by reacting the compound of formula (20-1)wherein A¹, A², A³, Y, R¹, R², n and J⁴ are as defined above that arethe compounds of formula (20) wherein W is oxygen atom with asulfurizing agent such as diphosphorus pentasulfide, diphosphoruspentasulfide-HMDO (hexamethyldisiloxane), Lawesson's Reagent(2,4-bis(4-methoxyphenyl)-1,3,2,4-dithiadiphosphetane-2,4-disulfide)under a condition similar to that of Production Method D.

In each reaction, after the completion of the reaction, each productionintermediate that is a starting compound in Production Method A toProduction Method C can be obtained by carrying out normalpost-treatments.

In addition, each production intermediate produced by theabove-mentioned methods can be used for the following reaction step assuch without isolation or purification.

The active compounds included in the present invention concretelyinclude for example the compounds shown in Tables 2 and 3. The compoundsthat can be used as novel production intermediates for producing theactive compounds included in the present invention concretely includefor example the compounds shown in Tables 4 to 6. In the interim, thecompounds shown in Tables 2 to 6 are for purposes of illustration andthe present invention is not limited thereto.

In the meantime, in Tables, the indication “Et” means ethyl, hereinaftersimilarly thereto, “n-Pr” and “Pr-n” mean normal propyl, “i-Pr” and“Pr-i” mean isopropyl, “c-Pr” and “Pr-c” mean cyclopropyl, “n-Bu” and“Bu-n” mean normal butyl, “s-Bu” and “Bu-s” mean secondary butyl, “i-Bu”and “Bu-i” mean isobutyl, “t-Bu” and “Bu-t” mean tertiary butyl, “c-Bu”and “Bu-c” mean cyclobutyl, “n-Pen” and “Pen-n” mean normal pentyl,“c-Pen” and “Pen-c” mean cyclopentyl, “n-Hex” and “Hex-n” mean normalhexyl, “c-Hex” and “Hex-c” mean cyclohexyl, “Hept” means heptyl, “Oct”means octyl, “Ph” means phenyl, “1-Naph” means 1-naphthyl, “2-Naph”means 2-naphthyl, and in Tables, aromatic heterocyclic rings of D-1a toD-65a are the following structures, respectively

For example, the indication “[CH₂(D-17a)CH₃]” means 1-methylpyrazol-5-ylmethyl, the indication “[CH₂(D-22b)CH₃] means 2-methylthiazol-4-ylmethyl.In addition, aliphatic heterocyclic rings of E-4a to E-43b are thefollowing structures, respectively

For example, the indication “[CH₂(E-10b)CH₃]” means2-methyl-1,3-dioxolan-2-yl methyl, the indication “[CH₂(E-8a)CH₃]” meansN-methylpyrrolidin-2-yl methyl. Further, in Tables, partially saturatedheterocyclic rings of M-2a to M-16a are the following structures,respectively

For example, the indication “[CH₂(M-5a)CH₃]” means3-methyl-4,5-dihydroisoxazol-5-yl methyl.Further, in Tables, T-1 to T-49 are the following structures,respectively

Lengthy table referenced here US20110251398A1-20111013-T00001 Pleaserefer to the end of the specification for access instructions.

Lengthy table referenced here US20110251398A1-20111013-T00002 Pleaserefer to the end of the specification for access instructions.

Lengthy table referenced here US20110251398A1-20111013-T00003 Pleaserefer to the end of the specification for access instructions.

Lengthy table referenced here US20110251398A1-20111013-T00004 Pleaserefer to the end of the specification for access instructions.

Lengthy table referenced here US20110251398A1-20111013-T00005 Pleaserefer to the end of the specification for access instructions.

The compounds of the present invention can effectively control in a lowconcentration so-called agricultural insects injuring agricultural andhorticultural crops and trees, so-called domestic animal pestsparasitizing domestic animals and domestic fowls, so-called hygienicpests having an adverse affect on human being's environment such ashouses, insects as so-called stored grain insects injuring grains andthe like stored in storehouses, and any pests of acarids, crustaceans,mollusks and nematodes generating in the similar scenes.

The insects, acarids, crustaceans, mollusks and nematodos that thecompounds of the present invention can control concretely include forexample the followings:

Lepidoptera insects, such as Adoxophyes honmai, Adoxophyes oranafaciata, Archips breviplicanus, Archips fuscocupreanus, Grapholitamolesta, Homona magnanima, Leguminivora glycinivorella, Matsumuraesesphaseoli, Pandemis heparana, Bucculatrix pyrivorella, Lyonetiaclerkella, Lyonetia prunifoliella malinella, Caloptilia theivora,Phyllonorycter ringoniella, Phyllocnistis citrella, Acrolepiopsissapporensis, Acrolepiopsis suzukiella, Plutella xylostella, Stathmopodamasinissa, Helcystogramma triannulella, Pectinophora gossypiella,Carposina sasakii, Cydla pomonella, Chilo suppressalis, Cnaphalocrocismedinalis, Conogethes punctiferalis, Diaphania indica, Etiellazinckenella, Glyphodes pyloalis, Hellula undalis, Ostrinia furnacalis,Ostrinia scapulalis, Ostrinia nubilalis, Parapediasia teterrella,Parnara guttata, Pieris brassicae, Pieris rapae crucivora, Ascotisselenaria, Pseudoplusia includens, Euproctis pseudoconspersa, Lymantriadispar, Orgyia thyellina, Hyphantria cunea, Lemyra imparilis, Adristyrannus, Aedia leucomelas, Agrotis ipsilon, Agrotis segetum, Autographanigrisigna, Ctenoplusia agnata, Helicoverpa armigera, Helicoverpaassulta, Helicoverpa zea, Heliothis virescens, Mamestra brassicae,Mythimna separata, Naranga aenescens, Spodoptera eridania, Spodopteraexigua, Spodoptera frugiperda, Spodoptera littoralis, Spodoptera litura,Spodoptera depravata, Trichoplusia ni, Endopiza viteana, Manducaquinquemaculata, Manduca sexta, or the like;Thysanoptera insects, such as Frankliniella intonsa, Frankliniellaoccidentalis, Heliothrips haemorrhoidalis, Scirtothrips dorsalis, Thripspalmi, Thrips tabaci, Ponticulothrips diospyrosi, or the like;Hemiptera insects, such as Dolycoris baccarum, Eurydema rugosum,Eysarcoris aeneus, Eysarcoris lewisi, Eysarcoris ventralis, Glauciassubpunctatus, Halyomorpha halys, Nezara antennata, Nezara viridula,Piezodorus hybneri, Plautia crossota, Scotinophora lurida, Cletuspunctiger, Leptocorisa chinensis, Riptortus clavatus, Rhopalusmsculatus, Cavelerius saccharivorus, Togo hemipterus, Dysdercuscingulatus, Stephanitis pyrioides, Halticus insularis, Lygus lineolaris,Stenodema sibiricum, Stenotus rubrovittatus, Trigonotylus caelestialium,Arboridia apicalis, Balclutha saltuella, Epiacanthus stramineus,Empoasca fabae, Empoasca nipponica, Empoasca onukii, Empoasca sakaii,Macrosteles striifrons, Nephotettix cinctinceps, Psuedatomoscelisseriatus, Laodelphax striatella, Nilaparvata lugens, Sogatellafurcifera, Diaphorina citri, Psylla pyrisuga, Aleurocanthus spiniferus,Bemisia argentifolii, Bemisia tabaci, Dialeurodes citri, Trialeurodesvaporariorum, Viteus vitifolii, Aphis gossypii, Aphis spiraecola, Myzuspersicae, Toxoptera aurantii, Drosicha corpulenta, lcerya purchasi,Phenacoccus solani, Planococcus citri, Planococcus kuraunhiae,Pseudococcus comstocki, Ceroplastes ceriferus, Ceroplastes rubens,Aonidiella aurantii, Comstockaspis perniciosa, Fiorinia theae,Pseudaonidia paeoniae, Pseudaulacaspis pentagona, Pseudaulacaspisprunicola, Unaspis euonymi, Unaspis yanonensis, Cimex lectularius, orthe like;Coleoptera insects, such as Anomala cuprea, Anomala rufocuprea, Gametisjucunda, Heptophylla picea, Popillia japonica, Lepinotarsa decemlineata,Melanotus fortnumi, Melanotus tamsuyensis, Lasioderma serricorne,Epuraea domina, Epilachna varivestis, Epilachna vigintioctopunctata,Tenebrio molitor, Tribolium castaneum, Anoplophora malasiaca, Monochamusalternatus, Psacothea hilaris, Xylotrechus pyrrhoderus, Callosobruchuschinensis, Aulacophora femoralis, Chaetocnema concinna, Diabroticaundecimpunctata, Diabrotica virgifera, Diabrotica barberi, Oulemaoryzae, Phyllotreta striolata, Psylliodes angusticollis, Rhynchitesheros, Cylas formicarius, Anthonomus grandis, Echinocnemus squameus,Euscepes postfasciatus, Hypera postica, Lissohoptrus oryzophilus,Otiorhynchus sulcatus, Sitophilus granarius, Sitophilus zeamais,Sphenophorus venatus vestitus, Paederus fuscipes, or the like;Diptera insects, such as Asphondylia yushimai, Sitodiplosis mosellana,Bactrocera cucurbitae, Bactrocera dorsalis, Ceratitis capitata,Hydrellia griseola, Drosophila suzukii, Agromyza oryzae, Chromatomyiahorticola, Liriomyza bryoniae, Liriomyza chinensis, Liriomyza sativae,Liriomyza trifolii, Delia platura, Pegomya cunicularia, Rhagoletispomonella, Mayetiola destructor, Musca domestica, Stomoxys calcitrans,Melophagus ovinus, Hypoderma bovis, Hypoderma lineatum, Oestrus ovis,Glossina palpalis, Glossina morsitans, Prosimulium yezoensis, Tabanustrigonus, Telmatoscopus albipunctatus, Leptoconops nipponensis, Culexpipiens pallens, Aedes aegypti, Aedes albopicutus, Anopheles hyracanussinesis, or the like;Hymenoptera insects, such as Apethymus kuri, Athalia rosae, Arge pagana,Neodiprion sertifer, Dryocosmus kuriphilus, Eciton burchelli, Ecitonschmitti, Camponotus japonicus, Vespa mandarina, Myrmecia spp.,Solenopsis spp., Monomorium pharaonis, or the like;Orthoptera insects, such as Teleogryllus emma, Gryllotalpa orientalis,Locusta migratoria, Oxya yezoensis, Schistocerca gregaria, or the like;Collembola insects, such as Onychiurus folsomi, Onychiurus sibiricus,Bourletiella hortensis, or the like;Dictyoptera insect, such as Periplaneta fuliginosa, Periplanetajaponica, Blattella germanica, or the like;Isoptera insects, such as Coptotermes formosanus, Reticulitermessperatus, Odontotermes formosanus, or the like;Siphonaptera insects, such as Ctenocephalidae felis, Ctenocephalidescanis, Echidnophaga gallinacea, Pulex irritans, Xenopsylla cheopis, orthe like;Mallophaga insects, such as Menacanthus stramineus, Bovicola bovis, orthe like;Anoplura insects, such as Haematopinus eurysternus, Haematopinus suis,Linognathus vituli, Solenopotes capillatus, or the like;Tarsonemid mites, such as Phytonemus pallidus, Polyphagotarsonemuslatus, Tarsonemus bilobatus, or the like;Eupodid mites, such as Penthaleus erythrocephalus, Penthaleus major, orthe like;Spider mites, such as Oligonychus shinkajii, Panonychus citri,Panonychus mori, Panonychus ulmi, Tetranychus kanzawai, Tetranychusurticae, or the like;Eriophyid mites, such as Acaphylla theavagrans, Aceria tulipae, Aculopslycopersici, Aculops pelekassi, Aculus schlechtendali, Eriophyeschibaensis, Phyllocoptruta oleivora, or the like;Acarid mites, such as Rhizoglyphus robini, Tyrophagus putrescentiae,Tyrophagus similis, or the like;Bee brood mites, such as Varroa jacobsoni, or the like;Ixodides, such as Boophilus microplus, Rhipicephalus sanguineus,Haemaphysalis longicornis, Haemophysalis flava, Haemophysaliscampanulata, Ixodes ovatus, Ixodes persulcatus, Amblyomma spp.,Dermacentor spp., or the like;Cheyletidae, such as Cheyletiella yasguri, Cheyletiella blakei, or thelike;Demodicidae, such as Demodex canis, Demodex cati, or the like;Psoroptidae, such as Psoroptes ovis, or the like;Scarcoptidae, such as Sarcoptes scabiei, Notoedres cati, Knemidocoptesspp., or the like;Crustacea, such as Armadillidium vulgare, or the like;Gastropoda, such as Pomacea canaliculata, Achatina fulica, Meghimatiumbilineatum, Limax Valentiana, Acusta despecta sieboldiana, Euhadrapeliomphala, or the like;Nematodes, such as Prathylenchus coffeae, Prathylenchus penetrans,Prathylenchus vulnus, Globodera rostochiensis, Heterodera glycines,Meloidogyne hapla, Meloidogyne incognita, Aphelenchoides besseyi,Bursaphelenchus xylophilus, or the like. But the present invention isnot limited thereto.

The endo-parasites of domestic animals, domestic fowls, pets and thelike that the compounds of the present invention can control concretelyinclude for example the followings:

Nematodes, such as Haemonchus, Trichostrongylus, Ostertagia,Nematodirus, Cooperia, Ascaris, Bunostomum, Oesophagostomum, Chabertia,Trichuris, Storongylus, Trichonema, Dictyocaulus, Capillaria, Heterakis,Toxocara, Ascaridia, Oxyuris, Ancylostoma, Uncinaria, Toxascaris,Parascaris, or the like; Filariidae in nematodes, such as Wuchereria,Brugia, Onchoceca, Dirofilaria, Loa, or the like;Dracunculidae in nematodes, such as Deacunculus, or the like;Cestoda, such as Dipylidium caninum, Taenia taeniaeformis, Taeniasolium, Taenia saginata, Hymenolepis diminuta, Moniezia benedeni,Diphyllobothrium latum, Diphyllobothrium erinacei, Echinococcusgranulosus, Echinococcus multilocularis, or the like;Trematoda, such as Fasciola hepatica, F. gigantica, Paragonimuswestermanii, Fasciolopsic bruski, Eurytrema pancreaticum, E.coelomaticum, Clonorchis sinensis, Schistosoma japonicum, Schistosomahaematobium, Schistosoma mansoni, or the like;Eimeria spp., such as Eimeria tenella, Eimeria acervulina, Eimeriabrunetti, Eimeria maxima, Eimeria necatrix, Eimeria bovis, Eimeriaovinoidalis, or the like;Trypanosomsa cruzi, Leishmania spp., Plasmodium spp., Babesis spp.,Trichomonadidae spp., Histomanas spp., Giardia spp., Toxoplasma spp.,Entamoeba histolytica, Theileria spp., or the like. But the presentinvention is not limited thereto.

Further, the compounds of the present invention are effective for pestsacquiring high resistance against existing insecticides such as organicphosphorus compounds, carbamate compounds or pyrethroid compounds, etc.

That is, the compounds of the present invention can effectively controlpests that belong to insects such as Collembola, Dictyoptera,Orthoptera, Isoptera, Thysanoptera, Hemiptera, Lepidoptera, Coleoptera,Hymenoptera, Diptera, Isoptera and Anoplura, Acarina, Gastropoda andNematoda, in a low concentration. On the other hand, the compounds ofthe present invention have an extremely useful characteristic that theyhave little adverse affect on mammals, fishes, crustaceans and usefulinsects (beneficial insect such as honeybee, bumblebee or the like, or,natural enemies such as Aphytis lingnanensis, Aphidius colemani, Oriusstrigicollis, Amblyseius californicus, or the like).

When the compounds of the present invention are used, they can begenerally mixed with a suitable solid carrier or liquid carrier,optionally along with surfactant, penetrating agent, spreading agent,thickener, anti-freezing agent, binder, anti-caking agent,disintegrating agent, anti-foaming agent, preservative, stabilizer, andthe like, and can be formulated into any desired forms for practicaluse, such as soluble concentrates, emulsifiable concentrates, wettablepowders, water soluble powders, water dispersible granules, watersoluble granules, suspension concentrates, concentrated emulsions,suspoemulsions, microemulsions, dustable powders, granules, tablets andemulsifiable gels. From the viewpoint of an elimination or reduction oflabor and an improvement of safety, the formulations in any desiredforms described above may be included into a water-soluble bag made ofwater-soluble capsule or water-soluble film.

The solid carrier includes, for example, natural minerals such asquartz, calcite, sepiolite, dolomaite, chalk, kaolinite, pyrofilite,celicite, halocite, methahalocite, kibushi clay, gairome clay, potterystone, zeaklite, allophane, white sand, mica, talc, bentonite, activetedearth, acid china clay, pumice, attapulgite, zeolite and diatomaceousearth, etc., calcined products of natural minerals such as calcinedclay, perlite, white sand balloon (loam balloon), vermiculite,attapulgus clay and calcined diatomaceous earth, etc., inorganic saltssuch as magnesium carbonate, calcium carbonate, sodium carbonate, sodiumhydrogen carbonate, ammonium sulfate, sodium sulfate, magnesium sulfate,diammonium hydrogen phosphate, ammonium dihydrogen phosphate andpotassium chloride, etc., saccharides such as glucose, fructose, sucroseand lactose, etc., polysaccharides such as starch, powder cellulose anddextrin, etc., organic materials such as urea, urea derivatives, benzoicacid and a salt of benzoic acid, etc., plants such as wood powder, corkpowder, corn head stem, walnut shell and tobacco stem, etc., fly ash,white carbon (e.g., hydrated synthetic silica, anhydrous syntheticsilica and hydrated synthetic silicate, etc.) and fertilizers, etc.

As the liquid carrier, there may be mentioned, for example, aromatichydrocarbons such as xylene, alkyl(C₉ or C₁₀, etc.)benzene,phenylxylylethane and alkyl(C₁ or C₃, etc.)naphthalene, etc., aliphatichydrocarbons such as machine oil, normal paraffin, isoparaffin andnaphthene, etc., a mixture of aromatic hydrocarbons and aliphatichydrocarbons such as kerosene, etc., alcohols such as ethanol,isopropanol, cyclohexanol, phenoxyethanol and benzylalcohol, etc.,polyvalent alcohols such as ethylene glycol, propyleneglycol, diethyleneglycol, hexylene glycol, polyethylene glycol and polypropyleneglycol,etc., ethers such as propyl cellosolve, butyl cellosolve, phenylcellosolve, propyleneglycol monomethyl ether, propyleneglycol monoethylether, propyleneglycol monopropyl ether, propyleneglycol monobutyl etherand propyleneglycol monophenyl ether, etc., ketones such asacetophenone, cyclohexanone and -butyrolactone, etc., esters such asaliphatic acid methyl ester, dialkyl succinate, dialkyl glutamate,dialkyl adipate and dialkyl phthalate, etc., acid amides such asN-alkyl(C₁, C₈ or C₁₂, etc.)pyrrolidone, etc., oil and fats such assoybean oil, linseed oil, rapeseed oil, coconut oil, cottonseed oil andcaster oil, etc., dimethylsulfoxide and water.

These solid and liquid carriers may be used alone or in combination oftwo or more kinds in combination.

As the surfactant, there may be mentioned, for example, nonionicsurfactants such as polyoxyethylene alkyl ether, polyoxyethylene alkyl(mono- or di-)phenyl ether, polyoxyethylene (mono-, di- ortri-)styrylphenyl ether, polyoxyethylene polyoxypropylene blockcopolymer, polyoxyethylene fatty acid (mono- or di-)ester, sorbitanfatty acid ester, polyoxyethylene sorbitan fatty acid ester, casteroil-ethylene oxide adducts, acetylene glycol, acetylene alcohol,ethylene oxide adducts of acetylene glycol, ethylene oxide adducts ofacetylene alcohol and alkyl glycoside, etc., anionic surfactants such asalkyl sulfate, alkylbenzenesulfonate, lignine sulfonate,alkylsulfosuccinate, naphthalene sulfonate, alkylnaphthalene sulfonate,formalin condensate salt of naphthalene sulfonic acid, formalincondensate salt of alkylnaphthalene sulfonic acid, polyoxyethylene alkylether sulfate or phosphate, polyoxyethylene (mono- or di-)alkylphenylether sulfate or phosphate, polyoxyethylene (mono-, di- ortri-)styrylphenyl ether sulfate or phosphate, polycarboxylate (e.g.,polyacrylates, polymaleates and copolymer materials of maleic acid andolefin, etc.) and polystyrenesulfonate, etc., cationic surfactants suchas alkylamine salt and alkyl quaternary ammonium salt, etc., amphotericsurfactants such as amino acid type and betaine type, etc., siliconetype surfactants and fluorine type surfactants.

A content of these surfactants is not specifically limited, and it isdesirably in the range of 0.05 to 20 parts by weight in general based on100 parts by weight of the preparation according to the presentinvention. Also, these surfactants may be used alone or in combinationof two or more kinds in combination.

A dose of the compound of the present invention to be applied may varydepending on the place to be applied, time to be applied, method to beapplied, crops to cultivate, etc., and in general, it is suitable in anamount of about 0.005 to 50 kg or so per a hectare (ha) as an amount ofthe effective ingredient.

On the other hand, when the compound of the present invention is usedfor controlling ecto- or endo-parasites of mammals and birds as domesticanimals and pets, the effective amount of the compound of the presentinvention together with additives for formulations can be administeredthrough oral administration, parenteral administration such as injection(intramuscular, subcutaneous, intravenous, intraperitoneal) or the like;transdermal administration such as dipping, spray, bathing, washing,pouring-on and spotting-on, and dusting, or the like; transnasaladministration. The compound of the present invention can be alsoadministered through a formed product by use of a strip, a plate, aband, a collar, an ear mark, a limb band, a labe apparatus, or the like.In administration, the compound of the present invention can be formedin an arbitrary dosage form that is suited for the administration route.

The arbitrary dosage form includes solid preparations such as a dustablepowder, a granule, wettable powder, a pellete, a tablet, a bolus, acapsule, a formed product containing an active compound; liquidformulations such as an injectable liquid formulation, an oral liquidformulation, a liquid formulation used on skin or in body cavity;solution preparations such as a pour-on agent, a spot-on agent, aflowable agent, an emulsifiable concentrate; semi-solid preparationssuch as an ointment, gel or the like.

The solid preparations can be mainly used through oral administration ortransdermal administration by diluting with water or the like, or byenvironmental treatment. The solid preparations can be prepared bymixing the active compound with suitable excipients and optionallyauxiliary substances and converting to a desired form. The suitableexcipients include for example inorganic substances such as carbonates,hydrogen carbonates, phosphates, aluminum oxide, silica, clay or thelike, organic substances such as sugar, cellulose, milled cereal, starchor the like.

The injectable liquid formulation can be administered intravenously,intramuscularly and subcutaneously. The injectable liquid formulationcan be prepared by dissolving an active compound in a suitable solventand optionally by adding an additive such as a solubilizing agent, anacid, a base, a buffering salt, an antioxidant, and a protective agentor the like. Suitable solvent is for example water, ethanol, butanol,benzyl alcohol, glycerin, propylene glycol, poethylene glycol,N-methylpyrrolidone, and a mixture thereof, a physiologicallypermissible vegetable oil, a synthetic oil suitable for injection, orthe like. The solubilizing agent includes polyvinyl pyrrolidone,polyoxyethylated castor oil and polyoxyethylated sorbitan ester, or thelike. The protective agent includes benzyl alcohol, trichlorobutanol,p-hydroxybenzoic acid ester and n-butanol or the like.

The oral liquid formulation can be administered directly or afterdilution. It can be prepared similarly to the injectable liquidformulation.

The flowable agent and the emulsifiable concentrate can be administereddirectly or after dilution through transdermal administration orenvironmental treatment.

The liquid formulation used on skin can be administered by pouring on,spreading, rubbing, atomizing, spraying, or dipping (dipping, bathing orwashing). These liquid can be prepared similarly to the injectableliquid formulation.

The pour-on agent and the spot-on agent are poured or atomized on thelimited spot on the skin, thereby the active compound can be penetratedinto the skin and act in the whole body. The pour-on agent and thespot-on agent can be prepared by dissolving, suspending or emulsifyingan active ingredient in a suitable skin-fitted solvent or solventmixture. If required, an auxiliary substance such as a surfactant, acolorant, an absorption promoting agent, an antioxidant, a lightstabilizer and an adhesive, etc. may be added.

Suitable solvent includes water, alkanol, glycol, polyethylene glycol,polypropylene glycol, glycerin, benzyl alcohol, phenylethanol,phenoxyethanol, ethyl acetate, butyl acetate, benzyl benzoate,dipropylene glycol monomethyl ether, diethylene glycol monobutyl ether,acetone, methyl ethyl ketone, aromatic and/or aliphatic hydrocarbon,vegetable or synthetic oil, DMF, liquid paraffin, light-duty liquidparaffin, silicone, dimethylacetamide, N-methylpyrrolidone or2,2-dimethyl-4-oxy-methylene-1,3-dioxolane. The absorption promotingagent includes DMSO, isopropyl myristate, dipropylene glycolpelargonate, silicone oil, aliphatic ester, triglyceride and fattyalcohol. The antioxidant includes sulfite, metabisulfite, ascorbic acid,butylhydroxytoluene, butylhydroxyanisole and tocopherol.

The emulsifiable concentrate can be administrated orally, subcutaneouslyor injectably. The emulsifiable concentrate can be prepared bydissolving an active ingredient in a hydrophobic phase or a hydrophilicphase, and then homogenating the resulting solution with a suitableemulsifying agent optionally with further an auxiliary substance such asa colorant, an absorption promoting agent, a protective agent, anantioxidant, a light screen and a thickening agent.

The hydrophobic phase (oil) includes paraffin oil, silicone oil,sesame-seed oil, oil of almonds, castor oil, synthetic triglyceride,ethyl stearate, di-n-butyryl adipate, hexyl laurate, dipropylene glycolpelargonate, ester of branched short chain length aliphatic acid withsaturated aliphatic acid of chain length C16 to C18, isopropylmyristate, isopropyl palmitate, capryl/caprylic acid ester of saturatedfatty alcohol of chain length C12 to C18, isopropyl stearate, oleyloleate, decyl oleate, ethyl oleate, ethyl lactate, wax-like fatty acidester, dibutyl phthalate, diisopropyl adipate, isotridecyl alcohol,2-octyldodecanol, cetylstearyl alcohol, oleyl alcohol.

The hydrophilic phase includes water, propylene glycol, glycerin,sorbitol.

The emulsifying agent includes non-ionic surfactants such aspolyoxyethylated castor oil, polyoxyethylated sorbitan mono-olefinate,sorbitan monostearate, glycerin monostearate, polyoxyethyl stearate,alkylphenol polyglycol ether; amphoteric surfactants such as di-sodiumN-lauryl-iminodipropionate, lecithin or the like; anionic surfactantssuch as sodium lauryl sulfate, fatty alcohol sulfuric acid ether,monoethanol amine salt of mono/dialkylpolyglycol orthophosphate or thelike; cationic surfactants such as cetyl chloride trimethylammonium orthe like.

The other auxiliary substance includes carbocymethylcellulose,methylcellulose, polyacrylate, arginate, gelatin, gum arabic, polyvinylpyrrolidone, polyvinyl alcohol, methylvinyl ether, copolymer of maleicanhydride, polyethylene glycol, wax, colloidal silica.

The semi-solid preparation can be administered by coating or spreadingon the skin, or by introducing in body cavity. The gel can be preparedby adding a thickener in an amount enough to provide a clear substancehaving a viscosity of ointment in a solution prepared for the injectableliquid formulation as mentioned above.

Next, formulation examples of the preparation in case where the compoundof the present invention is used are shown below. Provided thatformulation examples of the present invention are not limited onlythereto. In the interim, in the following Formulation Examples,“part(s)” mean part(s) by weight.

(Wettable Powder)

Compound of the present invention 0.1 to 80 parts Solid carrier 5 to98.9 parts Surfactant 1 to 10 parts Others 0 to 5 partsAs other components, there may be mentioned, for example, a non-cakingagent, a decomposition preventing agent, and the like.

(Emulsifiable Concentrate)

Compound of the present invention 0.1 to 30 parts Liquid carrier 45 to95 parts Surfactant 4.9 to 15 parts Others 0 to 10 partsAs other components, there may be mentioned, for example, a spreadingagent, a decomposition preventing agent, and the like.

(Suspension Concentrate)

Compound of the present invention 0.1 to 70 parts Liquid carrier 15 to98.89 parts Surfactant 1 to 12 parts Others 0.01 to 30 partsAs other components, there may be mentioned, for example, anantifreezing agent, a thickening agent, and the like.

(Water Dispersible Granule)

Compound of the present invention 0.1 to 90 parts Solid carrier 0 to98.9 parts Surfactant 1 to 20 parts Others 0 to 10 partsAs other components, there may be mentioned, for example, a binder, adecomposition preventing agent, and the like.

(Soluble Concentrate)

Compound of the present invention 0.01 to 70 parts Liquid carrier 20 to99.99 parts Others 0 to 10 partsAs other components, there may be mentioned, for example, anantifreezing agent, a spreading agent, and the like.

(Granule)

Compound of the present invention 0.01 to 80 parts Solid carrier 10 to99.99 parts Others 0 to 10 partsAs other components, there may be mentioned, for example, a binder, adecomposition preventing agent, and the like.

(Dustable Powder)

Compound of the present invention 0.01 to 30 parts Solid carrier 65 to99.99 parts Others 0 to 5 partsAs other components, there may be mentioned, for example, a driftpreventing agent, a decomposition preventing agent, and the like.

Next, formulation examples using the compound of the present inventionas an effective ingredient are described in more detail, but the presentinvention is not limited thereto. In the interim, in the followingFormulation Examples, “part(s)” mean part(s) by weight.

Formulation Example 1 Wettable Powder

Compound of the present invention No. 5-075 20 parts Pyrophylite 74parts Solpol 5039  4 parts (A mixture of a nonionic surfactant and ananionic surfactant: available from TOHO Chemical Industry Co., LTD,Tradename) CARPREX #80D  2 parts (Synthetic hydrated silicic acid:available from Shionogi & Co., Ltd., Tradename)The above materials are uniformly mixed and pulverized to make wettablepowder.

Formulation Example 2 Emulsion

Compound of the present invention No. 5-075  5 parts Xylene 75 partsN-methylpyrrolidone 15 parts Solpol 2680  5 parts (A mixture of anonionic surfactant and an anionic surfactant: available from TOHOChemical Industry Co., LTD, Tradename)The above materials are uniformly mixed to make emulsifiableconcentrate.

Formulation Example 3 Suspension Concentrate

Compound of the present invention No. 5-075 25 parts Agrisol S-710 10parts (a nonionic surfactant: available from KAO CORPORATION, Tradename)Lunox 1000C 0.5 part (an anionic surfactant: available from TOHOChemical Industry Co., LTD, Tradename) Xanthan gum 0.2 part Water 64.3partsThe above materials are uniformly mixed, and then, wet pulverized tomake suspension concentrate.

Formulation Example 4 Water Dispersible Granule

Compound of the present invention No. 5-075 75 parts HITENOL NE-15  5parts (an anionic surfactant: available from DAI-ICHI KOGYO SEIYAKU CO.,LTD., Tradename) VANILLEX N 10 parts (an anionic surfactant: availablefrom Nippon Paper Chemicals Co., Ltd., Tradename) CARPREX #80D 10 parts(Synthetic Hydrated Silicic Acid: Available from Shionogi & Co., Ltd.,Tradename)The above materials are uniformly mixed and pulverized, and then, asmall amount of water is added to the mixture and the resulting mixtureis mixed under stirring, granulated by an extrusion granulator, anddried to make water dispersible granule.

Formulation Example 5 Granule

Compound of the present invention No. 5-075  5 parts Bentonite 50 partsTalc 45 partsThe above materials are uniformly mixed and pulverized, and then, asmall amount of water is added to the mixture and the resulting mixtureis mixed under stirring, granulated by an extrusion granulator, anddried to make granule.

Formulation Example 6 Dustable Powder

Compound of the present invention No. 5-075   3 parts CARPREX #80D 0.5parts (Synthetic hydrated silicic acid: available from Shionogi & Co.,Ltd., Tradename) Kaolinite  95 parts Diisopropyl phosphate 1.5 partsThe above materials are uniformly mixed and pulverized to make dustablepowder. When the formulation is used, it is sprayed by diluting withwater in 1- to 1000-fold concentration, or directly without dilution.

Formulation Example 7 Wettable Powder Preparation

Compound of the present invention No. 5-086 25 parts Sodiumdiisobutylnaphthalenesulfonate 1 part Calcium n-dodecylbenzenesulfonate10 parts Alkylaryl polyglycol ether 12 parts Sodium salt ofnaphthalenesulfonic acid formalin condensate 3 parts Emulsion typesilicone 1 part Silicon dioxide 3 parts Kaoline 45 parts

Formulation Example 8 Water-Soluble Concentrate Preparation

Compound of the present invention No. 5-086 20 parts Polyoxyethylenelauryl ether 3 parts Sodium dioctylsulfosuccinate 3.5 partsDimethylsulfoxide 37 parts 2-Propanol 36.5 parts

Formulation Example 9 Liquid Formulation for Atomization

Compound of the present invention No. 5-086  2 parts Dimethylsulfoxide10 parts 2-Propanol 35 parts Acetone 53 parts

Formulation Example 10 Liquid Formulation for Transdermal Administration

Compound of the present invention No. 5-086  5 parts Hexylene glycol 50parts Isopropanol 45 parts

Formulation Example 11 Liquid Formulation for Transdermal Administration

Compound of the present invention No. 5-086  5 parts Propylene glycolmonomethyl ether 50 parts Dipropylene glycol 45 parts

Formulation Example 12 Liquid Formulation for Transdermal Administration(Pouring-on)

Compound of the present invention No. 5-086  2 parts Light-duty liquidparaffin 98 parts

Formulation Example 13 Liquid Formulation for Transdermal Administration(Pouring-on)

Compound of the present invention No. 5-086  2 parts Light-duty liquidparaffin 58 parts Olive oil 30 parts ODO-H  9 parts Shinetsu silicone  1part

Also, when the compound of the present invention is used as anagricultural chemicals, it may be mixed with other kinds of herbicides,various kinds of insecticides, acaricides, nematocides, fungicides,vegetable growth regulators, synergists, fertilizers, soil improvers,etc., and applied, at the time of preparing the formulation or at thetime of spreading, if necessary.

In particular, by mixing with the other agricultural chemicals or planthormones and applying the mixture, it can be expected that a cost isreduced due to reduction in a dose to be applied, enlargement ininsecticidal spectrum or higher prevention and extinction effect ofnoxious organisms due to synergistic effect by mixing agriculturalchemicals. At this time, it is possible to use the compound with aplural number of the conventionally known agricultural chemicals incombination simultaneously. As the kinds of the agricultural chemicalsto be used in admixture with the compound of the present invention,there may be mentioned, for example, the compounds described in FarmChemicals Handbook, 1999 ed. and the like. Specific examples of thegeneral names can be enumerated below, but the invention is notnecessarily limited only thereto.

Fungicides: acibenzolar-S-methyl, acylaminobenzamide, amobam,ampropylos, anilazine, azaconazole, azoxystrobin, benalaxyl, benodanil,benomyl, benthiazole, benzamacril, binapacryl, biphenyl, bitertanol,bethoxazine, bordeaux mixture, blasticidin-S, bromoconazole, bupirimate,buthiobate, calcium polysulfide, captafol, captan, copper oxychloride,carpropamid, carbendazim, carboxin, CGA-279202 (test name),chinomethionat, chlobenthiazone, chlorfenazol, chloroneb,chlorothalonil, chlozolinate, cufraneb, cymoxanil, cyproconazol,cyprodinil, cyprofuram, dazomet, debacarb, dichlorophen, diclobutrazol,diclhlofluanid, diclomedine, dicloran, diethofencarb, diclocymet,difenoconazole, diflumetorim, dimethirimol, dimethomorph, diniconazole,diniconazole-M, dinocap, diphenylamine, dipyrithione, ditalimfos,dithianon, dodemorph, dodine, drazoxolon, edifenphos, epoxiconazole,etaconazole, ethirimol, etridiazole, famoxadone, fenarimol,febuconazole, fenamidone, fendazosulam, fenfuram, fenhexamid,fenpiclonil, fenpropidin, fenpropimorph, fentin, ferbam, ferimzone,fluazinam, fludioxonil, fluoroimide, fluquinconazole, flusilazole,flusulfamide, flutolanil, flutriafol, folpet, fosetyl-aluminium,fuberidazole, furalaxyl, furametpyr, guazatine, hexachlorobenzene,hexaconazole, hymexazol, imazalil, imibenconazole, iminoctadine,ipconazole, iprobenfos, iprodione, isoprothiolane, iprovalicarb,kasugamycin, kresoxim-methyl, mancopper, mancozeb, maneb, mepanipyrim,mepronil, metalaxyl, metconazole, methasulfocarb, metiram,metominostrobin, myclobutanil, MTF-753 (test name), nabam, nickelbis(dimethyldithiocarbamate), nitrothal-isopropyl, nuarimol, NNF-9425(test name), octhilinone, ofurace, oxadixyl, oxycarboxin, oxpoconazolefumarate, pefurzoate, penconazole, pencycuron, phthalide, piperalin,polyoxins, potassium hydrogen carbonate, probenazole, prochloraz,procymidone, propamocarb hydrochloride, propiconazole, propineb,pyrazophos, pyrifenox, pyrimethanil, pyroquilon, quinomethionate,quinoxyfen, quintozene, RH 7281 (test name), sodium hydrogen carbonate,sodium hypochlorite, sulfur, spiroxamine, tebuconazole, tecnazene,tetraconazole, thiabendazole, thiadiazin/milneb, thifluzamide,thiophanate-methyl, thiram, tolclofos-methyl, tolylfluanid, triadimefon,toriadimenol, triazoxide, tricyclazole, tridemorph, triflumizole,triforine, triticonazole, validamycin, vinclozolin, zinc sulfate, zineb,ziram, and shiitake mushroom hyphae extract, etc.;Bactericides: streptomycin, tecloftalam, oxyterracycline, and oxolinicacid, etc.;Nematocides: aldoxycarb, cadusafos, fosthiazate, fosthietan, oxamyl, andfenamiphos, etc.;Acaricides: acequinocyl, amitraz, bifenazate, bromopropylate,chinomethionat, chlorobezilate, clofentezine, cyhexatine, dicofol,dienochlor, etoxazole, fenazaquin, fenbutatin oxide, fenpropathrin,fenproximate, halfenprox, hexythiazox, milbemectin, propargite,pyridaben, pyrimidifen, and tebufenpyrad, etc.;Insecticides: abamectin, acephate, acetamipirid, aldicarb, allethrin,azinphos-methyl, bendiocarb, benfuracarb, bensultap, bifenthrin,buprofezin, butocarboxim, carbaryl, carbofuran, carbosulfan, cartap,chlorfenapyr, chlorpyrifos, chlorfenvinphos, chlorfluazuron,clothianidin, chromafenozide, chlorpyrifos-methyl, cycloprothrin,cyfluthrin, beta-cyfluthrin, cypermethrin, cyromazine, cyhalothrin,lambda-cyhalothrin, deltamethrin, diafenthiuron, diazinon, diacloden,diflubenzuron, dimethylvinphos, diofenolan, disulfoton, dimethoate,emamectin-benzoate, EPN, esfenvalerate, ethiofencarb, ethiprole,etofenprox, etrimfos, fenitrothion, fenobucarb, fenoxycarb,fenpropathrin, fenvalerate, fipronil, fluacrypyrim, flucythrinate,flufenoxuron, flufenprox, tau-fluvalinate, fonophos, formetanate,formothion, furathiocarb, halofenozide, hexaflumuron, hydramethylnon,imidacloprid, isofenphos, indoxacarb, isoprocarb, isoxathion, lufenuron,malathion, metaldehyde, methamidophos, methidathion, methacrifos,metalcarb, methomyl, methoprene, methoxychlor, methoxyfenozide,monocrotophos, muscalure, nidinotefuran, nitenpyram, omethoate,oxydemeton-methyl, oxamyl, parathion, parathion-methyl, permethrin,phenthoate, phoxim, phorate, phosalone, phosmet, phosphamidon,pirimicarb, pirimiphos-methyl, profenofos, protrifenbute, pymetrozine,pyraclofos, pyriproxyfen, rotenone, sulprofos, silafluofen, spinosad,sulfotep, tebfenozide, teflubenzuron, tefluthorin, terbufos,tetrachlorvinphos, thiacloprid, thiocyclam, thiodicarb, thiamethoxam,thiofanox, thiometon, tolfenpyrad, tralomethrin, trichlorfon, triazuron,triflumuron, and vamidothion, etc.

EXAMPLES

Hereinafter, the present invention will be explained in more detail byspecifically referring to Synthetic Examples and Test Examples of thecompound of the present invention as working examples to which thepresent invention is not limited.

Synthetic Examples Synthetic Example 1 Production of the Compound of thePresent Invention by Use of L-Cos (Parallel Liquid-Phase SynthesisSystem of Moritex Corporation)

In 15 bials of L-COS in which stirrers were placed, 1.5 mmol of eachn-propylamine, i-propylamine, s-butylamine, t-butylamine, n-pentylamine,2,2-dimethylpropylamine, n-hexylamine, cyclohexylamine, benzylamine,4-trifluoromethylbenzylamine, 1-phenylethylamine, 2-phenylethylamine,2-(4-phenoxyphenyl)ethylamine, 3-phenylpropylamine andtrans-2-phenylcyclopropylamine was weighed, each bial was covered andplaced in a reaction vessel of L-COS. With stirring at room temperature,in each bial, 5 ml of a solution of4-[5-(3,4-dichlorophenyl)-5-trifluoromethyl-4,5-dihydroisoxazol-3-yl]benzoicacid in N,N-dimethylformamide-chloroform (1:3) (0.2 mmol/ml), 1 ml of asolution of 4-(dimethylamino)pyridine in chloroform (0.25 mmol/ml), andthen 1.5 ml of a solution of1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride inchloroform (1.0 mmol/ml) were added in that order, and continued to stirat the same temperature for 16 hours. After the completion of thereaction, 3 ml of cold water was added in each bials, and the organicphases were collected, and subjected to purification withmedium-pressure preparative liquid chromatography (Yamazen Corporation,medium pressure preparative system; YFLC-Wprep) that was eluted withethyl acetate-hexane (1:3 to 1:1 gradient), and the aimed product wasobtained as white to yellow solid. In addition, the product wasconfirmed with LC-MS (Waters LC-MS system, detector: ZMD, analysiscondition: 254 nm, 80% CH₃CN-20% H₂O-0.1% HCOOH, ionization: positiveelectrospray).

-   4-[5-(3,4-dichlorophenyl)-5-trifluoromethyl-4,5-dihydroisoxazol-3-yl]-N-n-propylbenzoic    acid amide; 0.26 g, [M⁺+H]=444.94.-   4-[5-(3,4-dichlorophenyl)-5-trifluoromethyl-4,5-dihydroisoxazol-3-yl]-N-i-propylbenzoic    acid amide; 0.23 g, [M⁺+H]=444.94.-   N-s-butyl-4-[5-(3,4-dichlorophenyl)-5-trifluoromethyl-4,5-dihydroisoxazol-3-yl]benzoic    acid amide; 0.20 g, [M⁺+H]=458.93.-   N-t-butyl-4-[5-(3,4-dichlorophenyl)-5-trifluoromethyl-4,5-dihydroisoxazol-3-yl]benzoic    acid amide; 0.21 g, [M⁺+H]=458.92.-   4-[5-(3,4-dichlorophenyl)-5-trifluoromethyl-4,5-dihydroisoxazol-3-yl]-N-n-pentylbenzoic    acid amide; 0.31 g, [M⁺+H]=473.02.-   4-[5-(3,4-dichlorophenyl)-5-trifluoromethyl-4,5-dihydroisoxazol-3-yl]-N-(2,2-dimethyl    propyl)benzoic acid amide; 0.27 g, [M⁺+H]=472.94.-   4-[5-(3,4-dichlorophenyl)-5-trifluoromethyl-4,5-dihydroisoxazol-3-yl]-N-n-hexylbenzoic    acid amide; 0.26 g, [M⁺+H]=486.96.-   N-cyclohexyl-4-[5-(3,4-dichlorophenyl)-5-trifluoromethyl-4,5-dihydroisoxazol-3-yl]benzoic    acid amide; 0.26 g, [M⁺+H]=484.93.-   N-benzyl-4-[5-(3,4-dichlorophenyl)-5-trifluoromethyl-4,5-dihydroisoxazol-3-yl]benzoic    acid amide; 0.34 g, [M⁺+H]=492.86.-   4-[5-(3,4-dichlorophenyl)-5-trifluoromethyl-4,5-dihydroisoxazol-3-yl]-N-(4-trifluoromethylbenzyl)benzoic    acid amide; 0.34 g, [M⁺+H]=560.97.-   4-[5-(3,4-dichlorophenyl)-5-trifluoromethyl-4,5-dihydroisoxazol-3-yl]-N-(1-phenylethyl)benzoic    acid amide; 0.26 g, [M⁺+H]=506.88.-   4-[5-(3,4-dichlorophenyl)-5-trifluoromethyl-4,5-dihydroisoxazol-3-yl]-N-(2-phenylethyl)benzoic    acid amide; 0.37 g, [M⁺+H]=507.01.-   4-[5-(3,4-dichlorophenyl)-5-trifluoromethyl-4,5-dihydroisoxazol-3-yl]-N-[2-(4-phenoxy    phenyl)ethyl]benzoic acid amide; 0.36 g, [M⁺+H]=598.95.-   4-[5-(3,4-dichlorophenyl)-5-trifluoromethyl-4,5-dihydroisoxazol-3-yl]-N-(3-phenylpropyl)benzoic    acid amide; 0.31 g, [M⁺+H]=520.97.-   4-[5-(3,4-dichlorophenyl)-5-trifluoromethyl-4,5-dihydroisoxazol-3-yl]-N-(trans-2-phenylcyclopropyl)benzoic    acid amide; 0.21 g, [M⁺+H]=518.88.

Synthetic Example 2 Production of the Compound of the Present Inventionby Use of L-Cos (Parallel Liquid-Phase Synthesis System of MoritexCorporation)

Ten (10) bials of L-COS in which stirrers were placed were assigned anumber of 1 to 10, respectively. 1.0 mmol of 3-chloro-4-fluorophenylboric acid was weighed in the bials of Nos. 1 and 6, 1.0 mmol of3,5-bis(trifluoromethyl)phenyl boric acid was weighed in the bials ofNos. 2 and 7, 1.0 mmol of 3-trifluoromethylphenyl boric acid was weighedin the bials of Nos. 3 and 8, 1.0 mmol of 3-trifluoromethoxyphenyl boricacid was weighed in the bials of Nos. 4 and 9, and 1.0 mmol of2-naphthyl boric acid was weighed in the bials of Nos. 5 and 10, Then,0.05 mmol of dichlorobis(triphenylphosphine) palladium (II) was added ineach bial, the bial was filled with nitrogen and covered, and placed ina reaction vessel of L-COS. With stirring at room temperature, in eachbial, 3 ml of a solution of 2-bromo-3,3,3-trifluoropropene in1,2-dimethoxyethane (0.5 mmol/ml), 1.5 ml of water, and then 1 ml of asolution of triethylamine in 1,2-dimethoxyethane (6.0 mmol/ml) wereadded in that order, and stirred at 75° C. for 3.5 hours. Then, thebials were cooled to 0° C., 1.5 ml of a solution ofN-benzyl-4-(chlorohydroxyiminomethyl)benzoic acid amide in1,2-dimethoxyethane (0.7 mmol/ml) was added in the bials of Nos. 1 to 5,and 1.5 ml of a solution of4-chlorohydroxyiminomethyl-N-(2,2,2-trifluoroethyl)benzoic acid amide in1,2-dimethoxyethan (0.7 mmol/ml) was added in the bials of Nos. 6 to 10,and the bials were continued to stir at room temperature for 16 hours.After the completion of the reaction, the organic phase was collected,aqueous phase was extracted with 5 ml of chloroform, the chloroform wasadded to the organic phase, and the solvent was distilled off underreduced pressure. The residue was subjected to purification withmedium-pressure preparative liquid chromatography (Yamazen Corporation,medium pressure preparative system; YFLC-Wprep) that was eluted withethyl acetate-hexane (1:3 to 1:1 gradient), and the aimed product wasobtained as white to yellow solid. In addition, the product wasconfirmed with LC-MS (Waters LC-MS system, detector: ZMD, analysiscondition: 254 nm, 80% CH₃CN-20% H₂O-0.1% HCOOH, ionization: positiveelectrospray).

-   N-benzyl-4-[5-(3-chloro-4-fluorophenyl)-5-trifluoromethyl-4,5-dihydroisoxazol-3-yl]benzoic    acid amide; 0.28 g, [M⁺+H]=476.80.-   N-benzyl-4-[5-[3,5-bis(trifluoromethyl)phenyl]-5-trifluoromethyl-4,5-dihydroisoxazol-3-yl]benzoic    acid amide; 0.25 g, [M⁺+H]=560.76.-   N-benzyl-4-[5-(3-trifluoromethylphenyl)-5-trifluoromethyl-4,5-dihydroisoxazol-3-yl]benzoic    acid amide; 0.26 g, [M⁺+H]=492.82.-   N-benzyl-4-[5-(3-trifluoromethoxyphenyl)-5-trifluoromethyl-4,5-dihydroisoxazol-3-yl]benzoic    acid amide; 0.25 g, [M⁺+H]=508.80.-   N-benzyl-4-[5-(2-naphthyl)-5-trifluoromethyl-4,5-dihydroisoxazol-3-yl]benzoic    acid amide; 0.09 g, [M⁺+H]=474.86.-   4-[5-(3-chloro-4-fluorophenyl)-5-trifluoromethyl-4,5-dihydroisoxazol-3-yl]-N-(2,2,2-trifluoroethyl)benzoic    acid amide; 0.29 g, [M⁺+H]=468.76.-   4-[5-[3,5-bis(trifluoromethyl)phenyl]-5-trifluoromethyl-4,5-dihydroisoxazol-3-yl]-N-(2,2,2-trifluoroethyl)benzoic    acid amide; 0.29 g, [M⁺+H]=552.72.-   4-[5-(3-trifluoromethylphenyl)-5-trifluoromethyl-4,5-dihydroisoxazol-3-yl]-N-(2,2,2-trifluoroethyl)benzoic    acid amide; 0.18 g, [M⁺+H]=484.78.-   4-[5-(3-trifluoromethoxyphenyl)-5-trifluoromethyl-4,5-dihydroisoxazol-3-yl]-N-(2,2,2-trifluoroethyl)benzoic    acid amide; 0.27 g, [M⁺+H]=500.76.-   4-[5-(2-naphthyl)-5-trifluoromethyl-4,5-dihydroisoxazol-3-yl]-N-(2,2,2-trifluoroethyl)benzoic    acid amide; 0.14 g, [M⁺+H]=466.83.

Synthetic Example 34-[5-(3,5-Dichlorophenyl)-5-trifluoromethyl-4,5-dihydroisoxazol-3-yl]-N-(2,2,2-trifluoroethyl)benzoicacid amide (Compound of the Present Invention No. 3-060) Step 1:Production of 3,5-dichloro-1-(1-trifluoromethylethenyl)benzene

In a solution of 25.0 g of 3,5-dichlorophenyl boric acid in 200 ml oftetrahydrofuran and 100 ml of water, 27.5 g of2-bromo-3,3,3-trifluoropropene, 38.0 g of potassium carbonate and 1.84 gof dichlorobis(triphenylphosphine) palladium (II) were added, andstirred under reflux with heat for 3 hours. After the completion of thereaction and cooling to room temperature, 500 ml of ice water was added,and extracted with ethyl acetate (500 ml×1). The organic phase waswashed with water, dried over anhydrous sodium sulfate, the solvent wasdistilled off under reduced pressure. The residue was purified withsilica gel column chromatography that was eluated with hexane, and 25.7g of the aimed product was obtained as colorless oily substance.

¹H NMR (CDCl₃, Me₄Si, 300 MHz) 7.41 (t, J=2.0 Hz, 1H), 7.3-7.35 (m, 2H),6.05 (q, J=3.2 Hz, 1H), 5.82 (q, J=3.2 Hz, 1H).

Step 2: Production of4-[5-(3,5-dichlorophenyl)-5-trifluoromethyl-4,5-dihydroisoxazol-3-yl]benzoicacid methyl ester

In a solution of 2.70 g of 4-(hydroxyiminomethyl)benzoic acid methylester in 15 ml of N,N-dimethylformamide, 2.04 g of N-chlorosuccinic acidimide was added, and stirred at 40° C. for 40 minutes. Then, thereaction mixture was cooled to 0° C., 3.40 g of3,5-dichloro-1-(1-trifluoromethylethenyl)benzene and 1.72 g oftriethylamine were added, continued to stir at room temperature for 18hours. After the completion of the reaction, the reaction mixture waspoured into 100 ml of ice water, extracted with ethyl acetate (50 ml×2),the organic phase was washed with water, dehydrated with saturatedsodium chloride aqueous solution and dried over anhydrous sodiumsulfate, and then the solvent was distilled off under reduced pressure.The residual solid was subjected to purification with medium-pressurepreparative liquid chromatography (Yamazen Corporation, medium pressurepreparative system; YFLC-Wprep) that was eluted with ethylacetate-hexane (1:1 to 1:3 gradient), and 4.05 g of the aimed productwas obtained as white crystal. Melting point 94.0 to 96.0° C.

¹H NMR (CDCl₃, Me₄Si, 300 MHz) δ 8.10 (d, J=8.4 Hz, 2H), 7.74 (d, J=8.4Hz, 2H), 7.43 (s, 2H), 7.26 (s, 1H), 4.12 (d, J=17.3 Hz, 1H), 3.94 (s,3H), 3.74 (d, J=17.3 Hz, 1H).

Step 3: Production of4-[5-(3,5-dichlorophenyl)-5-trifluoromethyl-4,5-dihydroisoxazol-3-yl]benzoicacid

In a solution of 3.99 g of4-[5-(3,5-dichlorophenyl)-5-trifluoromethyl-4,5-dihydroisoxazol-3-yl]benzoicacid methyl ester in 50 ml of methanol, a solution of 2.00 g ofpotassium hydroxide in 25 ml of water was added, stirred at roomtemperature for 3 days and then at 40° C. for 5 hours. After thecompletion of the reaction, the reaction mixture was cooled with ice,and poured in 200 ml of water, and adjusted to pH 1-2 with concentratedhydrochloric acid, and then extracted with ethyl acetate (50 ml×2), theorganic phase was washed with water, dehydrated with saturated sodiumchloride aqueous solution and dried over anhydrous sodium sulfate, andthen the solvent was distilled off under reduced pressure to obtain 3.87g of the aimed product as pale yellow crystal.

Melting point 237.0 to 240.0° C.

¹H NMR (CDCl₃-DMSO-d₆, Me₄Si, 300 MHz) δ 8.09 (d, J=8.4 Hz, 2H), 7.76(d, J=8.4 Hz, 2H), 7.54 (s, 2H), 7.44 (s, 1H), 4.18 (d, J=17.7 Hz, 1H),3.86 (d, J=17.7 Hz, 1H).

Step 4: Production of4-[5-(3,5-dichlorophenyl)-5-trifluoromethyl-4,5-dihydroisoxazol-3-yl]-N-(2,2,2-trifluoroethyl)benzoic acid amide

In a suspension of 1.00 g of4-[5-(3,5-dichlorophenyl)-5-trifluoromethyl-4,5-dihydroisoxazol-3-yl]benzoicacid in 10 ml of benzene, 0.44 g of thionyl chloride and a catalyticamount (2 to 3 drops) of N,N-dimethylformamide were added, and stirredunder reflux with heat for 2.5 hours. After the completion of thereaction, the solvent was distilled off under reduced pressure to obtain1.81 g of crude4-[5-(3,5-dichlorophenyl)-5-trifluoromethyl-4,5-dihydroisoxazol-3-yl]benzoicacid chloride as pale yellow oily substance.

In a solution of 0.29 g of 2,2,2-trifluoroethylamine and 0.37 g oftriethylamine in 20 ml of chloroform, 1.81 g of the crude4-[5-(3,5-dichlorophenyl)-5-trifluoromethyl-4,5-dihydroisoxazol-3-yl]benzoicacid chloride dissolved in 10 ml of chloroform was added dropwise withcooling with ice and with stirring. After the completion of additiondropwise, the mixture was continued to stir at room temperature furtherfor 30 minutes. After the completion of the reaction, the reactionmixture was poured in 100 ml of water, and extracted with chloroform (20ml×3), the organic phase was washed with water, dehydrated withsaturated sodium chloride aqueous solution and dried over anhydroussodium sulfate, and passed through a glass filter packed with silicagel, and then the solvent was distilled off under reduced pressure. Theresidual solid was washed with hexane to obtain 1.05 g of the aimedproduct as white crystal. Melting point 94.0 to 96.0° C.

¹H NMR (CDCl₃, Me₄Si, 300 MHz) δ 7.86 (d, J=8.4 Hz, 2H), 7.76 (d, J=8.4Hz, 2H), 7.51 (s, 2H), 7.44 (s, 1H), 6.47 (t, J=6.3 Hz, 1H), 4.14 (qd,J=18.5, 6.3 Hz, 2H), 4.11 (d, J=17.4 Hz, 1H), 3.73 (d, J=17.4 Hz, 1H).

Synthetic Example 4N-Benzyl-4-[5-(3,5-dichlorophenyl)-5-trifluoromethyl-4,5-dihydroisoxazol-3-yl]-2-fluorobenzoic acid amide (Compound of the Present Invention No. 5-039) Step 1:Production of3-(4-bromomethyl-3-fluorophenyl)-5-(3,5-dichlorophenyl)-5-trifluoromethyl-4,5-dihydroisoxazole

In a solution of 1.50 g of5-(3,5-dichlorophenyl)-3-(3-fluoro-4-methylphenyl)-5-trifluoromethyl-4,5-dihydroisoxazolesynthesized from 3-fluoro-4-methylphenylaldoxime and3,5-dichloro-1-(1-trifluoromethylethenyl)benzene similarly to Step 2 ofSynthetic Example 3 in 50 ml of 1,2-dichloroethane, 0.68 g ofN-bromosuccinic acid imide and a catalytic amount ofazobisisobutyronitrile were added, and stirred under nitrogen atmosphereand under reflux with heat for 1 hour. After the completion of thereaction, the reaction mixture was left and cooled to room temperature,poured in 50 ml of water, extracted with chloroform (50 ml×1). Theorganic phase was dehydrated with saturated sodium chloride aqueoussolution and dried over anhydrous sodium sulfate, and then the solventwas distilled off under reduced pressure to obtain crude aimed productas pale yellow oily substance. The resulting product was used as suchwithout purification for the next step.

¹H NMR (CDCl₃, Me₄Si, 400 MHz) δ 7.45-7.6 (m, 6H), 4.51 (s, 2H), 4.05(d, J=17.2 Hz, 1H), 3.67 (d, J=17.2 Hz, 1H).

Step 2: Production of3-(4-acetoxymethyl-3-fluorophenyl)-5-(3,5-dichlorophenyl)-5-trifluoromethyl-4,5-dihydroisoxazole

In a solution of crude3-(4-bromomethyl-3-fluorophenyl)-5-(3,5-dichlorophenyl)-5-trifluoromethyl-4,5-dihydroisoxazolein 30 ml of acetic acid, 1.50 g of potassium acetate was added, andstirred under reflux with heat for 1.5 hour. After the completion of thereaction, the reaction mixture was left and cooled to room temperature,and neutralized by pouring in 100 ml of saturated sodium hydrogencarbonate aqueous solution. The organic phase was collected, dehydratedwith saturated sodium chloride aqueous solution and dried over anhydroussodium sulfate, and then the solvent was distilled off under reducedpressure to obtain 1.50 g of crude aimed product as pale yellow oilysubstance. The resulting product was used as such without purificationfor the next step.

¹H NMR (CDCl₃, Me₄Si, 400 MHz) δ 7.2-7.55 (m, 6H), 5.20 (s, 2H), 4.05(d, J=17.2 Hz, 1H), 3.67 (d, J=17.2 Hz, 1H), 2.14 (s, 3H).

Step 3: Production of5-(3,5-dichlorophenyl)-3-(3-fluoro-4-hydroxymethylphenyl)-5-trifluoromethyl-4,5-dihydroisoxazole

In a solution of 1.50 g of crude3-(4-acetoxymethyl-3-fluorophenyl)-5-(3,5-dichlorophenyl)-5-trifluoromethyl-4,5-dihydroisoxazolein 10 ml of ethanol, 2.00 g of sodium hydroxide dissolved in 20 ml ofwater was added, and stirred under reflux with heat for 4.5 hours. Afterthe completion of the reaction, the reaction mixture was cooled withice, and adjusted to pH 2-3 by carefully adding concentratedhydrochloric acid, and extracted with ethyl acetate (50 ml×1). Theorganic phase was dehydrated with saturated sodium chloride aqueoussolution and dried over anhydrous sodium sulfate, and then the solventwas distilled off under reduced pressure. The residue was purified withsilica gel column chromatography that was eluated with ethylacetate-hexane (1:2) to obtain 0.95 g of the aimed product as paleyellow resinous substance.

¹H NMR (CDCl₃, Me₄Si, 400 MHz) δ 7.5-7.6 (m, 3H), 7.4-7.45 (m, 3H), 4.81(s, 2H), 4.06 (d, J=17.2 Hz, 1H), 3.68 (d, J=17.2 Hz, 1H), 1.87 (bs,1H).

Step 4: Production of4-[5-(3,5-dichlorophenyl)-5-trifluoromethyl-4,5-dihydroisoxazol-3-yl]-2-fluorobenzoic acid

In a solution of 0.95 g of5-(3,5-dichlorophenyl)-3-(3-fluoro-4-hydroxymethylphenyl)-5-trifluoromethyl-4,5-dihydroisoxazole in 25 ml of acetone, Johnes' Reagent prepared from 1.50 gof chromic acid, 1.2 ml of concentrated sulfuric acid and 7 ml of waterwas added dropwise under cooling with ice and with stirring, after thecompletion of the addition dropwise, continued to stir at roomtemperature for further 1.5 hour. After the completion of the reaction,the reaction mixture was poured in 50 ml of water and extracted withdiethyl ether (50 ml×1). The organic phase was dehydrated with saturatedsodium chloride aqueous solution and dried over anhydrous sodiumsulfate, and then the solvent was distilled off under reduced pressure.The residual solid was washed with hexane to obtain 0.67 g of the aimedproduct as beige crystal.

Melting point 172.0 to 174.0° C.

¹H NMR (CDCl₃, Me₄Si, 300 MHz) δ 8.05-8.15 (m, 1H), 7.45-7.55 (m, 5H),4.08 (d, J=17.3 Hz, 1H), 3.71 (d, J=17.3 Hz, 1H).

Step 5: Production ofN-benzyl-4-[5-(3,5-dichlorophenyl)-5-trifluoromethyl-4,5-dihydroisoxazol-3-yl]-2-fluorobenzoic acid amide

In a solution of 0.15 g of4-[5-(3,5-dichlorophenyl)-5-trifluoromethyl-4,5-dihydroisoxazol-3-yl]-2-fluorobenzoic acid in 10 ml of dichloromethane, 0.3 ml of oxalyl chloride and2 drops of N,N-dimethylformamide were added at room temperature, andstirred at the same temperature for 10 minutes. After the completion ofthe reaction, the solvent was distilled off under reduced pressure, theremaining white solid was dissolved in 10 ml of chloroform, and 0.3 mlof benzylamine and then 0.3 ml of triethylamine were added under coolingwith ice, after the completion of the addition, continued to stir atroom temperature for further 20 minutes. After the completion of thereaction, 40 ml of water was poured in the reaction mixture, andextracted with ethyl acetate (50 ml×1). The organic phase was dehydratedwith saturated sodium chloride aqueous solution and dried over anhydroussodium sulfate, and then the solvent was distilled off under reducedpressure. The residue was purified with silica gel column chromatographythat was eluated with ethyl acetate-hexane (1:2) to obtain 0.14 g of theaimed product as white crystal.

Melting point 172.0 to 176.0° C.

¹H NMR (CDCl₃, Me₄Si, 400 MHz) δ 8.20 (t, J=8.0 Hz, 1H), 7.25-7.55 (m,10H), 7.05 (t, J=5.6 Hz, 1H), 4.68 (d, J=5.6 Hz, 2H), 4.07 (d, J=17.6Hz, 1H), 3.70 (d, J=17.6 Hz, 1H).

Synthetic Example 54-[5-(3,5-Dichlorophenyl)-5-trifluoromethyl-4,5-dihydroisoxazol-3-yl]-2-nitro-N-(2-pyridylmethyl)benzoicacid amide (Compound of the Present Invention No. 5-339) Step 1:Production of 4-bromo-3-nitrobenzaldoxime

In a solution of 5.0 g of 4-bromo-3-nitrobenzaldehyde in 50 ml ofmethanol, 3.6 ml of 50% hydroxyamine aqueous solution was added withstirring at room temperature, and continued to stir at the sametemperature for 18 hours. After the completion of the reaction, 60 ml ofwater was added in the reaction mixture, and precipitated solid wasfiltered off, washed with water and then dried to obtain 5.0 g of theaimed product as yellow crystal.

¹H NMR (CDCl₃-DMSO-d₆, Me₄Si, 400 MHz) δ 11.18 (s, 1H), 8.09 (s, 1H),8.07 (d, J=2.0 Hz, 1H), 7.73 (d, J=8.4 Hz, 1H), 7.62 (dd, J=8.4, 2.0 Hz,1H).

Step 2: Production of3-(4-bromo-3-nitrophenyl)-5-(3,5-dichlorophenyl)-5-trifluoromethyl-4,5-dihydroisoxazole

In a solution of 1.27 g of 4-bromo-3-nitrobenzaldoxime in 16 ml ofN,N-dimethylformamide, 0.74 g of N-chlorosuccinic acid imide was added,and stirred at 35° C. for 90 minutes. Then, the reaction mixture wascooled with ice, 1.20 g of3,5-dichloro-1-(1-trifluoromethylethenyl)benzene synthesized in Step 1of Synthetic Example 3 and 0.60 g of triethylamine were added, continuedto stir at room temperature for 18 hours. After the completion of thereaction, the reaction mixture was poured in 50 ml of ice water,extracted with ethyl acetate (50 ml×2), the organic phase was dehydratedwith saturated sodium chloride aqueous solution and dried over anhydroussodium sulfate, and then the solvent was distilled off under reducedpressure. The residual solid was subjected to purification withmedium-pressure preparative liquid chromatography (Yamazen Corporation,medium pressure preparative system; YFLC-Wprep) that was eluted withethyl acetate-hexane (1:2 to 1:4 gradient), and 1.10 g of the aimedproduct was obtained as yellow crystal.

Melting point 179.0 to 181.0° C.

¹H NMR (CDCl₃, Me₄Si, 400 MHz) δ 8.06 (d, J=2.0 Hz, 1H), 7.84 (d, J=8.4Hz, 1H), 7.78 (dd, J=8.4, 2.0 Hz, 1H), 7.45-7.55 (m, 2H), 7.45 (t, J=1.8Hz, 1H), 4.09 (d, J=17.2 Hz, 1H), 3.72 (d, J=17.4 Hz, 1H).

Step 3: Production of4-[5-(3,5-dichlorophenyl)-5-trifluoromethyl-4,5-dihydroisoxazol-3-yl]-2-nitrobenzoicacid ethyl ester

In a solution of 2.0 g of3-(4-bromo-3-nitrophenyl)-5-(3,5-dichlorophenyl)-5-trifluoromethyl-4,5-dihydroisoxazolein 30 ml of ethanol in an autoclave, 0.40 g of sodium acetate, 88.0 mgof 1,1′-bis(diphenylphosphino) ferrocene and 18.0 mg of palladium (II)acetate were added, and stirred under 0.9 MPa carbon monoxide atmosphereat 100° C. for 3 hours. After the completion of the reaction, thereaction mixture was left and cooled to room temperature, and thesolvent was distilled off under reduced pressure, and the residue wasdissolved in 100 ml of ethyl acetate, washed with water, dried overanhydrous sodium sulfate and the solvent was distilled off under reducedpressure. The residual solid was subjected to purification withmedium-pressure preparative liquid chromatography (Yamazen Corporation,medium pressure preparative system; YFLC-Wprep) that was eluted withethyl acetate-hexane (1:2 to 1:4 gradient), and 0.66 g of the aimedproduct was obtained as pale yellow crystal.

Melting point 160.0 to 162.0° C.

¹H NMR (CDCl₃, Me₄Si, 400 MHz) δ 8.13 (d, J=1.6 Hz, 1H), 7.99 (dd,J=8.1, 1.6 Hz, 1H), 7.83 (d, J=8.1 Hz, 1H), 7.45-7.55 (m, 2H), 7.45 (t,J=1.8 Hz, 1H), 4.41 (q, J=7.1 Hz, 2H), 4.11 (d, J=17.2 Hz, 1H), 3.74 (d,J=17.8 Hz, 1H), 1.37 (t, J=7.1 Hz, 3H).

Step 4: Production of4-[5-(3,5-dichlorophenyl)-5-trifluoromethyl-4,5-dihydroisoxazol-3-yl]-2-nitro-N-(2-pyridylmethyl)benzoicacid amide

In a solution of 0.36 g of4-[5-(3,5-dichlorophenyl)-5-trifluoromethyl-4,5-dihydroisoxazol-3-yl]-2-nitrobenzoicacid ethyl ester in 8 ml of ethanol, a solution of 0.40 g of potassiumhydroxide in 2 ml of water was added, and stirred at room temperaturefor 3 hours. After the completion of the reaction, the reaction mixturewas poured in 15 ml of water, adjusted to pH 4 with concentratedhydrochloric acid, then extracted with ethyl acetate (20 ml×2), theorganic phase was washed with water, and then dehydrated with saturatedsodium chloride aqueous solution and dried over anhydrous sodium sulfateand the solvent was distilled off under reduced pressure to obtain 0.40g of crude4-[5-(3,5-dichlorophenyl)-5-trifluoromethyl-4,5-dihydroisoxazol-3-yl]-2-nitrobenzoic acid as pale yellow oily substance. The substance was dissolvedin 10 ml of chloroform, and 0.24 g of 2-picolylamine, 0.01 g of4-(N,N-dimethylamino)pyridine and 0.35 g of1-[3-(diethylamino)propyl]-3-ethylcarbodiimide hydrochloride were added,and stirred at room temperature for 18 hours. After the completion ofthe reaction, the solvent was distilled off under reduced pressure. Theresidue was subjected to purification with medium-pressure preparativeliquid chromatography (Yamazen Corporation, medium pressure preparativesystem; YFLC-Wprep) that was eluted with ethyl acetate-hexane (1:1 to1:0 gradient), and 0.14 g of the aimed product was obtained as colorlessresinous substance.

¹H NMR (CDCl₃-DMSO-d₆, Me₄Si, 300 MHz) δ 8.50 (d, J=4.8 Hz, 1H), 8.25(d, J=1.7 Hz, 1H), 8.03 (dd, J=8.1, 1.6 Hz, 1H), 7.72 (td, J=7.7, 1.6Hz, 1H), 7.68 (d, J=8.1 Hz, 1H), 7.51 (d, J=1.5 Hz, 2H), 7.45 (t, J=1.8Hz, 1H), 7.43 (bs, 1H), 7.36 (d, J=7.9 Hz, 1H), 7.23 (dd, J=6.8, 5.3 Hz,1H), 4.76 (d, J=4.8 Hz, 2H), 4.13 (d, J=17.4 Hz, 1H), 3.76 (d, J=17.4Hz, 1H).

Synthetic Example 64-[5-(3,5-Dichlorophenyl)-5-trifluoromethyl-4,5-dihydroisoxazol-3-yl]-2-methoxy-N-(2,2,2-trifluoroethyl)benzoicacid amide (Compound of the Present Invention No. 5-317) Step 1:Production of 4-hydroxyiminomethyl-2-methoxyphenyl trifluoromethanesulfonate

In a solution of 3.0 g of 4-hydroxy-3-methoxybenzaldehyde and 2.4 g oftriethylamine in 50 ml of dichloromethane, 5.8 g of trifluoromethanesulfonic acid anhydride was added dropwise under cooling with ice andwith stirring, after the completion of the addition dropwise, continuedto stir at the same temperature for 30 minutes. After the completion ofthe reaction, the reaction mixture was washed with 50 ml of water andthen with 30 ml of saturated sodium hydrogen carbonate aqueous solution,and dehydrated with saturated sodium chloride aqueous solution and driedover anhydrous magnesium sulfate, and then the solvent was distilled offunder reduced pressure. The residue was dissolved in a mixture of 30 mlof ethanol and 15 ml of water, 1.4 g of hydroxyamine hydrochloride and1.7 g of sodium acetate were added with stirring at room temperature,and continued to stir at the same temperature for further 1 hour. Afterthe completion of the reaction, the solvent was distilled off underreduced pressure, extracted with ethyl acetate (40 ml×2), the organicphase was washed with water (30 ml×1), and then dehydrated withsaturated sodium chloride aqueous solution and dried over anhydrousmagnesium sulfate, and then the solvent was distilled off under reducedpressure to obtain 5.25 g of the aimed product as brown oily substance.

Refractive index n_(D) ^(20.2° C.)=1.5082

¹H NMR (CDCl₃-DMSO-d₆, Me₄Si, 300 MHz) δ 8.47 (bs, 1H), 8.11 (s, 1H),7.32 (s, 1H), 7.24 (d, J=8.1 Hz, 1H), 7.10 (d, J=8.1 Hz, 1H), 3.94 (s,3H).

Step 2: Production of4-[5-(3,5-dichlorophenyl)-5-trifluoromethyl-4,5-dihydroisoxazol-3-yl]-2-methoxyphenyltrifluoromethane sulfonate

In a solution of 2.0 g of 4-hydroxyiminomethyl-2-methoxyphenyltrifluoromethane sulfonate in 30 ml of N,N-dimethylformamide, 0.9 g ofN-chlorosuccinic acid imide was added, and stirred at 40 to 50° C. for30 minutes. Then, the reaction mixture was left and cooled to roomtemperature, 1.5 g of 3,5-dichloro-1-(1-trifluoromethylethenyl)benzenesynthesized in Step 1 of Synthetic Example 3 and 0.7 g of triethylaminewere added, and stirred at room temperature for 90 minutes. After thecompletion of the reaction, the reaction mixture was poured in 100 ml ofice water, extracted with ethyl acetate (50 ml×2), the organic phase wasdehydrated with saturated sodium chloride aqueous solution and driedover anhydrous magnesium sulfate, and then the solvent was distilled offunder reduced pressure. The residue was purified with silica gel columnchromatography that was eluated with ethyl acetate-hexane (1:7), and 1.4g of the aimed product was obtained as colorless resinous substance.

¹H NMR (CDCl₃, Me₄Si, 300 MHz) δ 7.50 (s, 2H), 7.44 (s, 1H), 7.25-7.3(m, 2H), 7.11 (d, J=8.4 Hz, 1H), 4.08 (d, J=17.1 Hz, 1H), 3.97 (s, 3H),3.69 (d, J=17.1 Hz, 1H).

Step 3: Production of4-[5-(3,5-dichlorophenyl)-5-trifluoromethyl-4,5-dihydroisoxazol-3-yl]-2-methoxybenzoic acid ethyl ester

In a solution of 1.50 g of4-[5-(3,5-dichlorophenyl)-5-trifluoromethyl-4,5-dihydroisoxazol-3-yl]-2-methoxyphenyltrifluoromethane sulfonate in 25 ml of ethanol in an autoclave, 0.27 gof sodium acetate, 31.0 mg of 1,1′-bis(diphenylphosphino) ferrocene and7.0 mg of palladium (II) acetate were added, and stirred under 0.96 MPacarbon monoxide atmosphere at 100° C. for 2 hours. After the completionof the reaction, the reaction mixture was left and cooled to roomtemperature, and the reaction mixture was poured in 100 ml of ice water,extracted with ethyl acetate (40 ml×2). The organic phases together weredehydrated with saturated sodium chloride aqueous solution and driedover anhydrous magnesium sulfate, and then the solvent was distilled offunder reduced pressure. The residue was purified with silica gel columnchromatography that was eluated with ethyl acetate-hexane (1:5), and1.20 g of the aimed product was obtained as white crystal.

Melting point 142.0-144.0° C.

¹H NMR (CDCl₃, Me₄Si, 300 MHz) δ 7.82 (d, J=7.8 Hz, 1H), 7.51 (s, 2H),7.4-7.45 (m, 2H), 7.10 (d, J=7.8 Hz, 1H), 4.37 (q, J=7.2 Hz, 2H), 4.10(d, J=17.4 Hz, 1H), 3.95 (s, 3H), 3.71 (d, J=17.4 Hz, 1H), 1.39 (t,J=7.2 Hz, 3H).

Step 4: Production of4-[5-(3,5-dichlorophenyl)-5-trifluoromethyl-4,5-dihydroisoxazol-3-yl]-2-methoxybenzoic acid

In a solution of 1.07 g of4-[5-(3,5-dichlorophenyl)-5-trifluoromethyl-4,5-dihydroisoxazol-3-yl]-2-methoxybenzoic acid ethyl ester in 30 ml of ethanol, a solution of 1.0 g ofsodium hydroxide in 30 ml of water was added, stirred at 85° C. for 1hour. After the completion of the reaction, the solvent was distilledoff under reduced pressure. The residue was adjusted to pH 2 to 3 withconcentrated hydrochloric acid, and extracted with ethyl acetate (30ml×2). The organic phase was dehydrated with saturated sodium chlorideaqueous solution and dried over anhydrous magnesium sulfate, and thenthe solvent was distilled off under reduced pressure to obtain 1.0 g ofthe aimed product as pale yellow resinous substance.

¹H NMR (CDCl₃, Me₄Si, 300 MHz) 10.67 (bs, 1H), 8.24 (d, J=7.8 Hz, 1H),7.57 (s, 1H), 7.51 (s, 2H), 7.45 (s, 1H), 7.22 (d, J=7.8 Hz, 1H),4.05-4.15 (m, 4H), 3.74 (d, J=17.4 Hz, 1H).

Step 5: Production of4-[5-(3,5-dichlorophenyl)-5-trifluoromethyl-4,5-dihydroisoxazol-3-yl]-2-methoxy-N-(2,2,2-trifluoroethyl)benzoicacid amide

In a suspension of 0.25 g of4-[5-(3,5-dichlorophenyl)-5-trifluoromethyl-4,5-dihydroisoxazol-3-yl]-2-methoxybenzoic acid in 15 ml of dichloromethane, 0.09 g of oxalyl chloride and1 drop of N,N-dimethylformamide were added, and stirred at roomtemperature for 1 hour. After the completion of the reaction, thesolvent was distilled off under reduced pressure, the residue wasdissolved in 15 ml of dichloromethane, and 0.09 g of triethylamine wasadded under cooling with ice, then 0.07 g of 2,2,2-trifluoroethylaminewas added dropwise. After the completion of addition dropwise, themixture was continued to stir at the same temperature for further 2hours. Thereafter, the reaction mixture was diluted with 60 ml ofchloroform, washed with 50 ml of water, then dehydrated with saturatedsodium chloride aqueous solution and dried over anhydrous sodiumsulfate, and then the solvent was distilled off under reduced pressure.The residue was purified with silica gel column chromatography that waseluated with ethyl acetate-hexane (1:2) to obtain 0.25 g of the aimedproduct as colorless resinous substance.

¹H NMR (CDCl₃, Me₄Si, 300 MHz) 8.2-8.3 (m, 2H), 7.51 (s, 3H), 7.43 (s,1H), 7.17 (d, J=7.8 Hz, 1H), 4.05-4.2 (m, 3H), 4.05 (s, 3H), 3.74 (d,J=17.4 Hz, 1H).

Synthetic Example 74-[5-(4-Fluoro-3-methylphenyl)-5-trifluoromethyl-4,5-dihydroisoxazol-3-yl]-N-(2,2,2-trifluoroethyl)benzoicacid amide (Compound of the Present Invention No. 3-141) Step 1:Production of 4-formyl-N-(2,2,2-trifluoroethyl)benzoic acid amide

In a suspension of 1.00 g of 4-formyl benzoic acid in 15 ml of benzene,0.87 g of thionyl chloride and 2 drops of N,N-dimethylformamide wereadded, and stirred under reflux with heat for 2 hours. After thecompletion of the reaction, the reaction mixture was left and cooled toroom temperature, and the solvent was distilled off under reducedpressure to obtain 1.14 g of crude 4-formyl benzoic acid chloride aswhite crystal. In a solution of 0.66 g of 2,2,2-trifluoroethylamine and0.81 g of triethylamine in 6 ml of chlororform, the solution of 1.14 gof the crude 4-formyl benzoic acid chloride in 6 ml of chloroform wasadded dropwise under cooling with ice and with stirring, after thecompletion of the addition dropwise, continued to stir at roomtemperature for further 18 hours. After the completion of the reaction,the reaction mixture was added in 30 ml of water, extracted withchloroform (20 ml×3). The organic phase was washed with water, driedover anhydrous sodium sulfate, the solvent was distilled off underreduced pressure, the residual solid was washed with hexane to obtain1.32 g of the aimed product as white crystal. Melting point 83.0 to84.0° C.

¹H NMR (CDCl₃, Me₄Si, 400 MHz) 10.09 (s, 1H), 7.96 (bs, 4H), 6.80 (bs,1H), 4.05-4.25 (m, 2H).

Step 2: Production of4-hydroxyiminomethyl-N-(2,2,2-trifluoroethyl)benzoic acid amide

In a solution of 4.11 g of 4-formyl-N-(2,2,2-trifluoroethyl)benzoic acidamide in 30 ml of ethanol and 10 ml of water, 1.99 g of hydroxyaminehydrochloride and 2.51 g of anhydrous sodium acetate were added, stirredat room temperature for 3.5 hours. After the completion of the reaction,the reaction mixture was poured in 100 ml of water, and then extractedwith ethyl acetate (30 ml×3), the organic phase was washed with 50 ml ofsaturated sodium hydrogen carbonate aqueous solution, then dehydratedwith saturated sodium chloride aqueous solution and dried over anhydroussodium sulfate, and then the solvent was distilled off under reducedpressure. The residual solid was washed with hexane to obtain 3.92 g ofthe aimed product as white crystal.

Melting point 153.0 to 154.0° C.

¹H NMR (CDCl₃, Me₄Si, 400 MHz) 10.89 (s, 1H), 8.08 (s, 1H), 8.03 (bs,1H), 7.84 (d, J=8.2 Hz, 2H), 7.60 (d, J=8.2 Hz, 2H), 3.95-4.1 (m, 2H).

Step 3: Production of4-chlorohydroxyiminomethyl-(2,2,2-trifluoroethyl)benzoic acid amide

In a solution of 3.80 g of4-hydroxyiminomethyl-N-(2,2,2-trifluoroethyl)benzoic acid amide in 50 mlof tetrahydrofuran, 20 ml of 3N hydrochloric acid was added, 14 ml of 8%sodium hypochlorite aqueous solution was added dropwise with stirringunder ice cooling over 10 minutes, after the completion of additiondropwise, continued to stir at the same temperature for further 15minutes. After the completion of the reaction, the reaction mixture waspoured in 200 ml of water, extracted with ethyl acetate (30 ml×3), theorganic phase was dehydrated with saturated sodium chloride aqueoussolution and dried over anhydrous sodium sulfate, and the solvent wasdistilled off under reduced pressure. The residual solid was washed withhexane to obtain 4.15 g of the product as white crystal.

Melting point 158.0 to 160.0° C.

¹H NMR (CDCl₃, Me₄Si, 400 MHz) 12.03 (s, 1H), 8.05 (t, J=6.0 Hz, 1H),7.93 (bs, 4H), 3.95-4.15 (m, 2H).

Step 4: Production of4-[5-(4-fluoro-3-methylphenyl)-5-trifluoromethyl-4,5-dihydrooxazol-3-yl]-N-(2,2,2-trifluoroethyl)benzoicacid amide

In a solution of 0.21 g of 4-fluoro-3-methylphenyl boric acid and 0.23 gof 2-bromo-3,3,3-trifluoropropene in 6 ml of 1,2-dimethoxyethane and 2ml of water, 0.24 g of sodium carbonate and 0.05 g ofdichlorobis(triphenylphosphine) palladium (II) were added, stirred at75° C. for 3 hours. Then, the reaction mixture was left and cooled toroom temperature, then a solution of 0.25 g of4-chlorohydroxyiminomethyl-N-(2,2,2-trifluoroethyl)benzoic acid amide in4 ml of 1,2-dimethoxyethane was added, continued to stir at the sametemperature for further 18 hours. After the completion of the reaction,the reaction mixture was poured in 50 ml of water, extracted with ethylacetate (10 ml×3), the organic phase was dehydrated with saturatedsodium chloride aqueous solution and dried over anhydrous sodiumsulfate, and the solvent was distilled off under reduced pressure. Theresidual solid was purified with silica gel column chromatography thatwas eluated with chloroform to obtain 0.24 g of the product as whitecrystal.

Melting point 151.0 to 152.0° C.

¹H NMR (CDCl₃, Me₄Si, 400 MHz) 7.86 (d, J=8.4 Hz, 2H), 7.76 (d, J=8.4Hz, 2H), 7.35-7.5 (m, 2H), 7.0-7.15 (m, 1H), 6.39 (t, J=6.3 Hz, 1H),4.05-4.25 (m, 2H), 4.09 (d, J=17.3 Hz, 1H), 3.74 (d, J=17.3 Hz, 1H),2.32 (d, J=1.7 Hz, 3H).

Synthetic Example 84-[5-(3,5-Dichlorophenyl)-5-trifluoromethyl-4,5-dihydroisoxazol-3-yl]-2-methyl-N-(2,2,2-trifluoroethyl)benzoicacid amide (Compound of the Present Invention No. 5-075) Step 1:Production of 4-bromo-2-methyl-N-(2,2,2-trifluoroethyl)benzoic acidamide

In a solution of 5.00 g of 4-bromo-2-methyl benzoic acid and 3.45 g of2,2,2-trifluoroethylamine in 30 ml of N,N-dimethylformamide, 5.79 g of1-[3-(diethylamino)propyl]-3-ethylcarbodiimide hydrochloride was addedwith stirring at room temperature, and stirred at the same temperaturefor 1.5 hour. After the completion of the reaction, 80 ml of water wasadded, and precipitated crystal was filtered off, washed with water anddried to obtain 4.00 g of the aimed product as white crystal.

Melting point 124.0 to 125.5° C.

¹H NMR (CDCl₃, Me₄Si, 400 MHz) 7.40 (s, 1H), 7.36 (d, J=8.4 Hz, 1H),7.22 (d, J=8.4 Hz, 1H), 6.15 (bs, 1H), 4.0-4.15 (m, 2H), 2.39 (s, 3H).

Step 2: Production of 4-formyl-2-methyl-N-(2,2,2-trifluoroethyl)benzoicacid amide

In a solution of 1.00 g of4-bromo-2-methyl-N-(2,2,2-trifluoroethyl)benzoic acid amide in 15 ml oftetrahydrofuran under nitrogen atmosphere, 4.7 ml of n-butyl lithium(1.58M hexane solution) was added dropwise at −70° C. with stirring, andthen 0.4 ml of N,N-dimethylformamide were added dropwise. After stirringat the same temperature for 30 minutes, 10 ml of 1N hydrochloric acidand then 30 ml of water were added, and extracted with ethyl acetate (30ml×2). The organic phase was dehydrated with saturated sodium chlorideaqueous solution and dried over anhydrous magnesium sulfate, the solventwas distilled off under reduced pressure to obtain 0.80 g of the aimedproduct as pale yellow crystal.

Melting point 99.0 to 104.0° C.

¹H NMR (CDCl₃, Me₄Si, 400 MHz) 10.00 (s, 1H), 7.7-7.75 (m, 2H), 7.50 (d,J=7.5 Hz, 1H), 6.27 (bs, 1H), 4.05-4.2 (m, 2H), 2.49 (s, 3H).

Step 3: Production of4-hydroxyiminomethyl-2-methyl-N-(2,2,2-trifluoroethyl)benzoic acid amide

In a solution of 0.8 g of4-formyl-2-methyl-N-(2,2,2-trifluoroethyl)benzoic acid amide in 10 ml ofethanol and 5 ml of water, 0.3 g of hydroxyamine hydrochloride and 0.4 gof anhydrous sodium acetate were added with stirring at roomtemperature, and stirred at the same temperature for 30 minutes. Afterthe completion of the reaction, the solvent was distilled off underreduced pressure, and precipitated crystal was filtered off, washed withwater and dried to obtain 0.5 g of the aimed product as white crystal.

Melting point 190.5 to 194.0° C.

¹H NMR (CDCl₃-DMSO-d₆, Me₄Si, 400 MHz) 10.98 (s, 1H), 8.43 (bs, 1H),8.07 (s, 1H), 7.35-7.55 (m, 3H), 3.95-4.1 (m, 2H), 2.43 (s, 3H).

Step 4: Production of4-[5-(3,5-dichlorophenyl)-5-trifluoromethyl-4,5-dihydroisoxazol-3-yl]-2-methyl-N-(2,2,2-trifluoroethyl)benzoicacid amide

In a solution of 0.40 g of4-hydroxyiminomethyl-2-methyl-N-(2,2,2-trifluoroethyl)benzoic acid amidein 15 ml of N,N-dimethylformamide, 0.21 g of N-chlorosuccinic acid imidewas added, and stirred at 50° C. for 30 minutes. Then, the reactionmixture was left and cooled to room temperature, 0.34 g of3,5-dichloro-1-(1-trifluoromethylethenyl)benzene synthesized in Step 1of Synthetic Example 3 and 0.16 g of triethylamine were added, andstirred at room temperature for 18 hours. After the completion of thereaction, the reaction mixture was poured in 50 ml of ice water,extracted with ethyl acetate (50 ml×1), the organic phase was dehydratedwith saturated sodium chloride aqueous solution and dried over anhydroussodium sulfate, and then the solvent was distilled off under reducedpressure. The residue was purified with silica gel column chromatographythat was eluated with ethyl acetate-hexane (1:2), and 0.45 g of theaimed product was obtained as white crystal.

Melting point 155.5 to 157.0° C.

¹H NMR (CDCl₃, Me₄Si, 400 MHz) 7.4-7.55 (m, 6H), 6.13 (bs, 1H), 4.05-4.2(m, 3H), 3.71 (d, J=17.4 Hz, 1H), 2.45 (s, 3H).

Synthetic Example 94-[5-(3,5-Dichlorophenyl)-5-trifluoromethyl-4,5-dihydroisoxazol-3-yl]-2-methyl-N-(2-pyridylmethyl)benzoicacid amide (Compound of the Present Invention No. 5-234) Step 1:Production of 4-bromo-2-methyl-N-(2-pyridylmethyl)benzoic acid amide

In a solution of 3.0 g of 4-bromo-2-methyl benzoic acid in 30 ml ofdichloromethane, 2.7 g of oxalyl chloride and 3 drops ofN,N-dimethylformamide were added under cooling with ice with stirring,and stirred at room temperature for 1 hour. After the completion of thereaction, the solvent was distilled off under reduced pressure, theresidue was dissolved in 30 ml of dichloromethane, 2.1 g oftriethylamine and 2.0 g of 2-picolylamine were added under cooling withice with stirring, and continued to stir at room temperature for 3hours. After the completion of the reaction, 50 ml of water was added inthe reaction mixture, extracted with chloroform (50 ml×2), the organicphase was washed with water, dehydrated with saturated sodium chlorideaqueous solution and dried over anhydrous sodium sulfate, and then thesolvent was distilled off under reduced pressure. The residual solid waswashed with diisopropylether to obtain 3.7 g of the aimed product asyellow crystal.

Melting point 86.0 to 87.5° C.

¹H NMR (CDCl₃, Me₄Si, 300 MHz) 8.52 (d, J=4.8 Hz, 1H), 7.69 (td, J=7.8,1.8 Hz, 1H), 7.15-7.4 (m, 6H), 4.73 (d, J=4.8 Hz, 2H), 2.45 (s, 3H).

Step 2: Production of 4-formyl-2-methyl-N-(2-pyridylmethyl)benzoic acidamide

In a solution of 2.0 g of 4-bromo-2-methyl-N-(2-pyridylmethyl)benzoicacid amide in 20 ml of N,N-dimethylformamide in an autoclave, 0.67 g ofsodium formate and 0.10 g of dichlorobis(triphenylphosphine) palladium(II) were added, and stirred under 1.05 MPa carbon monoxide atmosphereat 110° C. for 3 hours. After the completion of the reaction, thereaction mixture was left and cooled to room temperature, and poured in100 ml of water, and extracted with ethyl acetate (50 ml×2). The organicphases together were dehydrated with saturated sodium chloride aqueoussolution and dried over anhydrous magnesium sulfate, and then thesolvent was distilled off under reduced pressure. The residue waspurified with silica gel column chromatography that was eluated withethyl acetate-hexane (9:1), and 0.50 g of the aimed product was obtainedas pale yellow crystal.

Melting point 79.5 to 83.0° C.

¹H NMR (CDCl₃, Me₄Si, 300 MHz) 10.02 (s, 1H), 8.54 (d, J=5.1 Hz, 1H),7.6-7.8 (m, 4H), 7.15-7.4 (m, 3H), 4.77 (d, J=4.8 Hz, 2H), 2.55 (s, 3H).

Step 3: Production of4-hydroxyiminomethyl-2-methyl-N-(2-pyridylmethyl)benzoic acid amide

In a solution of 0.50 g of 4-formyl-2-methyl-N-(2-pyridylmethyl)benzoicacid amide in 10 ml of ethanol and 5 ml of water, 0.18 g of hydroxyaminehydrochloride was added with stirring at room temperature, and stirredat the same temperature for 12 hours. After the completion of thereaction, solid was filtered off, ethanol was distilled off underreduced pressure, and 30 ml of saturated sodium hydrogen carbonateaqueous solution was added in the remaining aqueous solution. Theprecipitated crystal was filtered off, washed with water and dried toobtain 0.45 g of the aimed product as pale yellow crystal.

Melting point 159.5 to 161.0° C.

¹H NMR (CDCl₃-DMSO-d₆, Me₄Si, 300 MHz) 11.89 (bs, 1H), 8.56 (d, J=4.2Hz, 1H), 8.03 (s, 1H), 7.90 (bs, 1H), 7.77 (t, J=7.8 Hz, 1H), 7.47 (d,J=7.5 Hz, 1H), 7.0-7.35 (m, 4H), 4.76 (d, J=6.0 Hz, 2H), 2.36 (s, 3H).

Step 4: Production of4-[5-(3,5-dichlorophenyl)-5-trifluoromethyl-4,5-dihydroisoxazol-3-yl]-2-methyl-N-(2-pyridylmethyl)benzoicacid amide

In a solution of 0.45 g of4-hydroxyiminomethyl-2-methyl-N-(2-pyridylmethyl)benzoic acid amide in10 ml of N,N-dimethylformamide, 0.25 g of N-chlorosuccinic acid imidewas added, and stirred at 70° C. for 1 hour. Then, the reaction mixturewas left and cooled to room temperature, 0.41 g of3,5-dichloro-1-(1-trifluoromethylethenyl)benzene synthesized in Step 1of Synthetic Example 3 and 0.25 g of potassium hydrogen carbonate wereadded, and stirred at room temperature for 3 hours. After the completionof the reaction, the reaction mixture was poured in 50 ml of ice water,extracted with ethyl acetate (60 ml×1), the organic phase was dehydratedwith saturated sodium chloride aqueous solution and dried over anhydrousmagnesium sulfate, and then the solvent was distilled off under reducedpressure. The residue was purified with silica gel column chromatographythat was eluated with ethyl acetate-hexane (3:1), and 0.30 g of theaimed product was obtained as white crystal.

Melting point 131.0 to 135.5° C.

¹H NMR (CDCl₃, Me₄Si, 300 MHz) 8.53 (d, J=5.0 Hz, 1H), 7.65-7.75 (m,1H), 7.2-7.55 (m, 9H), 4.75 (d, J=4.9 Hz, 2H), 4.09 (d, J=17.3 Hz, 1H),3.71 (d, J=17.3 Hz, 1H), 2.50 (s, 3H).

Synthetic Example 104-[5-(3,5-Dichlorophenyl)-5-trifluoromethyl-4,5-dihydroisoxazol-3-yl]-N-(2-pyridylmethyl)-2-trifluoromethylbenzoic acid amide (Compound of the Present Invention No. 5-315) Step 1:Production of4-[5-(3,5-dichlorophenyl)-5-trifluoromethyl-4,5-dihydroisoxazol-3-yl]-2-iodobenzoic acid methyl ester

In a solution of 0.60 g of4-[5-(3,5-dichlorophenyl)-5-trifluoromethyl-4,5-dihydroisoxazol-3-yl]-2-iodobenzoic acid synthesized similarly to Steps 1 to 4 of Synthetic Example4 in 10 ml of methanol, 2 drops of concentrated sulfuric acid was added,and stirred under reflux with heat for 20 hours. After the completion ofthe reaction, the solvent was distilled off under reduced pressure, theresidue was neutralized with 10 ml of saturated sodium hydrogencarbonate aqueous solution, then extracted with ethyl acetate (10 ml×2).The organic phase was washed with water, dehydrated with saturatedsodium chloride aqueous solution and dried over anhydrous sodiumsulfate, and then the solvent was distilled off under reduced pressure.The residue was purified with silica gel column chromatography that waseluated with ethyl acetate-hexane (1:4), and 0.56 g of the aimed productwas obtained as colorless oily substance.

¹H NMR (CDCl₃, Me₄Si, 400 MHz) 8.22 (d, J=1.5 Hz, 1H), 7.85 (d, J=8.2Hz, 1H), 7.75-7.8 (m, 1H), 7.5-7.55 (m, 2H), 7.4-7.45 (m, 1H), 4.07 (d,J=17.7 Hz, 1H), 3.95 (s, 3H), 3.69 (d, J=17.2 Hz, 1H).

Step 2: Production of4-[5-(3,5-dichlorophenyl)-5-trifluoromethyl-4,5-dihydroisoxazol-3-yl]-2-trifluoromethylbenzoic acid methyl ester

In a solution of 0.51 g of4-[5-(3,5-dichlorophenyl)-5-trifluoromethyl-4,5-dihydroisoxazol-3-yl]-2-iodobenzoic acid methyl ester in 5 ml of N,N-dimethylformamide, 0.18 g ofcopper (I) iodide, 0.06 g of potassium fluoride and 0.27 g ofchlorodifluoro acetic acid methyl ester were added, and stirred at 120°C. for 5 hours. After the completion of the reaction, the reactionmixture was left and cooled to room temperature, 50 ml of water wasadded and extracted with ethyl acetate (50 ml×2). The organic phase waswashed with water, dehydrated with saturated sodium chloride aqueoussolution and dried over anhydrous sodium sulfate, and then the solventwas distilled off under reduced pressure. The residue was purified withsilica gel column chromatography that was eluated with ethylacetate-hexane (1:4), and 0.45 g of the aimed product was obtained aspale yellow oily substance.

¹H NMR (CDCl₃, Me₄Si, 400 MHz) 8.00 (d, J=1.1 Hz, 1H), 7.85-7.95 (m,2H), 7.5-7.55 (m, 2H), 7.4-7.45 (m, 1H), 4.12 (d, J=7.1 Hz, 1H), 3.96(s, 3H), 3.94 (d, J=7.8 Hz, 1H).

Step 3: Production of4-[5-(3,5-dichlorophenyl)-5-trifluoromethyl-4,5-dihydroisoxazol-3-yl]-2-trifluoromethylbenzoic acid

In a solution of 0.40 g of4-[5-(3,5-dichlorophenyl)-5-trifluoromethyl-4,5-dihydroisoxazol-3-yl]-2-trifluoromethylbenzoic acid methyl ester in 5 ml of methanol, a solution of 0.10 g ofsodium hydroxide in 2 ml of water was added, and stirred at roomtemperature for 18 hours. After the completion of the reaction, 10 ml ofwater was added in the reaction mixture, washed with 5 ml of toluene,aqueous phase was collected, adjusted to pH 1 to 2 with concentratedhydrochloric acid and then extracted with ethyl acetate (20 ml×2). Theorganic phase was washed with water, dehydrated with saturated sodiumchloride aqueous solution and dried over anhydrous sodium sulfate, andthen the solvent was distilled off under reduced pressure to obtain 0.34g of the aimed product as pale yellow resinous substance. The resultingproduct was used as such without purification for the next step.

Step 4: Production of4-[5-(3,5-dichlorophenyl)-5-trifluoromethyl-4,5-dihydroisoxazol-3-yl]-N-(2-pyridylmethyl)-2-trifluoromethylbenzoic acid amide

In a solution of 0.15 g of4-[5-(3,5-dichlorophenyl)-5-trifluoromethyl-4,5-dihydroisoxazol-3-yl]-2-trifluoromethylbenzoic acid in 3 ml of dichloromethane, 0.06 g of oxalyl chloride and 1drop of N,N-dimethylformamide were added under cooling with ice withstirring, and stirred at room temperature for 2 hours. After thecompletion of the reaction, the solvent was distilled off under reducedpressure, the residue was dissolved in 3 ml of dichloromethane, and asolution of 0.05 g of 2-picolylamine and 0.06 g of triethylamine in 1 mlof dichloromethane was added dropwise, after the completion of theaddition dropwise, continued to stir at room temperature for 3 hours.After the completion of the reaction, 5 ml of water was added in thereaction mixture, extracted with chloroform (5 ml×2). The organic phasewas washed with water, dehydrated with saturated sodium chloride aqueoussolution and dried over anhydrous sodium sulfate, and then the solventwas distilled off under reduced pressure. The residue was purified withsilica gel column chromatography that was eluated with ethylacetate-hexane (1:3), and 0.05 g of the aimed product was obtained aswhite crystal.

Melting point 69.0 to 70.0° C.

¹H NMR (CDCl₃, Me₄Si, 400 MHz) 8.5-8.55 (m, 1H), 7.95 (bs, 1H), 7.91 (d,J=1.9 Hz, 1H), 7.65-7.8 (m, 2H), 7.5-7.55 (m, 2H), 7.35-7.45 (m, 3H),7.26 (t, J=4.9 Hz, 1H), 4.77 (d, J=4.9 Hz, 2H), 4.11 (d, J=17.4 Hz, 1H),3.73 (d, J=17.2 Hz, 1H).

Synthetic Example 114-[5-(3,5-Dichlorophenyl)-5-trifluoromethyl-4,5-dihydroisoxazol-3-yl]-2-phenyl-N-(2-pyridylmethyl)benzoicacid amide (Compound of the Present Invention No. 5-344) Step 1:Production of4-[5-(3,5-dichlorophenyl)-5-trifluoromethyl-4,5-dihydroisoxazol-3-yl]-2-phenylbenzoic acid methyl ester

In a solution of 0.70 g of2-bromo-4-[5-(3,5-dichlorophenyl)-5-trifluoromethyl-4,5-dihydroisoxazol-3-yl]benzoicacid methyl ester synthesized similarly to Step 1 of Synthetic Example10 in 20 ml of tetrahydrofuran and 10 ml of water, 0.18 g of phenylboric acid, 0.39 g of potassium carbonate and 0.05 g ofdichlorobis(triphenylphosphine) palladium (II) were added, and stirredunder reflux with heat for 1.5 hour. After the completion of thereaction, the solvent was distilled off under reduced pressure, theresidue was poured in 30 ml of water, then extracted with ethyl acetate(50 ml×1). The organic phase was washed with water, dehydrated withsaturated sodium chloride aqueous solution and dried over anhydroussodium sulfate, and then the solvent was distilled off under reducedpressure. The residue was purified with silica gel column chromatographythat was eluated with ethyl acetate, and 0.78 g of the aimed product wasobtained as brown resinous substance.

¹H NMR (CDCl₃, Me₄Si, 400 MHz) 7.89 (d, J=8.4 Hz, 1H), 7.74 (dd, J=8.0,1.8 Hz, 1H), 7.62 (d, J=1.4 Hz, 1H), 7.51 (d, J=1.8 Hz, 2H), 7.35-7.45(m, 4H), 7.25-7.35 (m, 2H), 4.11 (d, J=16.8 Hz, 1H), 3.73 (d, J=16.8 Hz,1H), 3.65 (s, 3H).

Step 2: Production of4-[5-(3,5-dichlorophenyl)-5-trifluoromethyl-4,5-dihydroisoxazol-3-yl]-2-phenylbenzoic acid

In a solution of 0.78 g of4-[5-(3,5-dichlorophenyl)-5-trifluoromethyl-4,5-dihydroisoxazol-3-yl]-2-phenylbenzoic acid methyl ester in 15 ml of ethanol, a solution of 0.30 g ofsodium hydroxide in 15 ml of water was added, and stirred at 60° C. for3 hours. After the completion of the reaction, ethanol was distilled offunder reduced pressure, adjusted to pH 1 to 2 with 12N hydrochloricacid, and then extracted with ethyl acetate (50 ml×1). The organic phasewas washed with water, dehydrated with saturated sodium chloride aqueoussolution and dried over anhydrous sodium sulfate, and then the solventwas distilled off under reduced pressure to obtain 0.70 g of the aimedproduct as brown glass substance. The resulting product was used as suchwithout purification for the next step.

Step 3: Production of4-[5-(3,5-dichlorophenyl)-5-trifluoromethyl-4,5-dihydroisoxazol-3-yl]-2-phenyl-N-(2-pyridylmethyl)benzoicacid amide

In a solution of 0.3 g of4-[5-(3,5-dichlorophenyl)-5-trifluoromethyl-4,5-dihydroisoxazol-3-yl]-2-phenylbenzoic acid in 10 ml of chloroform, 0.3 ml of oxalyl chloride and acatalytic amount (2 to 3 drops) of N,N-dimethylformamide were added withstirring at room temperature, and stirred at the same temperature for 10minutes. After the completion of the reaction, the solvent was distilledoff under reduced pressure, the residue was dissolved in 10 ml ofchloroform, and under cooling with ice with stirring 0.3 ml of2-picolylamine and then 0.3 ml of triethylamine were added, andcontinued to stir at room temperature for 20 minutes. After thecompletion of the reaction, the reaction mixture was poured in 40 ml ofwater, extracted with ethyl acetate (50 ml×1). The organic phase waswashed with water, dehydrated with saturated sodium chloride aqueoussolution and dried over anhydrous sodium sulfate, and then the solventwas distilled off under reduced pressure. The residue was purified withsilica gel column chromatography that was eluated with ethylacetate-hexane (2:1), and 0.2 g of the aimed product was obtained aswhite crystal.

Melting point 194.0 to 198.0° C.

¹H NMR (CDCl₃, Me₄Si, 400 MHz) 8.3-8.35 (m, 1H), 7.25-7.8 (m, 12H),7.1-7.15 (m, 1H), 7.40 (d, J=7.8 Hz, 1H), 6.65-6.7 (m, 1H), 4.47 (d,J=5.0 Hz, 2H), 4.12 (d, J=17.0 Hz, 1H), 3.74 (d, J=17.0 Hz, 1H).

Synthetic Example 122-Amino-4-[5-(3,5-dichlorophenyl)-5-trifluoromethyl-4,5-dihydroisoxazol-3-yl]-N-(2,2,2-trifluoroethyl)benzoicacid amide (Compound of the Present Invention No. 5-329) Step 1:Production of2-amino-4-[5-(3,5-dichlorophenyl)-5-trifluoromethyl-4,5-dihydroisoxazol-3-yl]benzoicacid ethyl ester

In a solution of 0.60 g of4-[5-(3,5-dichlorophenyl)-5-trifluoromethyl-4,5-dihydroisoxazol-3-yl]-2-nitrobenzoic acid ethyl ester synthesized in Steps 1 to 3 of SyntheticExample 5 in 6 ml of ethyl acetate, 2.0 ml of water, 0.6 ml of aceticacid and 0.46 g of reduced iron were added, and stirred at 75° C. for 2hours. After the completion of the reaction, the organic phase wascollected, and the aqueous phase was extracted with ethyl acetate (10ml×2). The organic phases together were washed with water, dehydratedwith saturated sodium chloride aqueous solution and dried over anhydroussodium sulfate, and then the solvent was distilled off under reducedpressure to obtain 0.60 g of crude aimed product as brown oilysubstance. The resulting product was used as such without purificationfor the next step.

Step 2: Production of2-amino-4-[5-(3,5-dichlorophenyl)-5-trifluoromethyl-4,5-dihydroisoxazol-3-yl]benzoicacid

In a solution of 0.6 g of crude2-amino-4-[5-(3,5-dichlorophenyl)-5-trifluoromethyl-4,5-dihydroisoxazol-3-yl]benzoicacid ethyl ester in 7 ml of ethanol, a solution of 0.5 g of potassiumhydroxide in 2.0 ml of water was added, and stirred at room temperaturefor 18 hours. After the completion of the reaction, 20 ml of ice waterwas added in the reaction mixture, adjusted to pH 2 to 3 withconcentrated hydrochloric acid, and then extracted with ethyl acetate(20 ml×2). The organic phase was washed with water, dehydrated withsaturated sodium chloride aqueous solution and dried over anhydroussodium sulfate, and then the solvent was distilled off under reducedpressure to obtain 0.6 g of crude aimed product as yellow oilysubstance. The resulting product was used as such without purificationfor the next step.

Step 3: Production of2-amino-4-[5-(3,5-dichlorophenyl)-5-trifluoromethyl-4,5-dihydroisoxazol-3-yl]-N-(2,2,2-trifluoroethyl)benzoicacid amide

In a solution of 0.60 g of crude2-amino-4-[5-(3,5-dichlorophenyl)-5-trifluoromethyl-4,5-dihydroisoxazol-3-yl]benzoicacid in 6 ml of chloroform, 0.20 g of 2,2,2-trifluoroethylamine, 0.02 gof 4-(N,N-dimethylamino)pyridine and 0.33 g of1-[3-(diethylamino)propyl]-3-ethylcarbodiimide hydrochloride were added,and stirred at room temperature for 20 hours. After the completion ofthe reaction, the reaction mixture was subjected to purification withmedium-pressure preparative liquid chromatography (Yamazen Corporation,medium pressure preparative system; YFLC-Wprep) that was eluted withethyl acetate-hexane (1:4), and 0.14 g of the aimed product was obtainedas pale yellow crystal.

Melting point 78.0 to 79.0° C.

¹H NMR (CDCl₃, Me₄Si, 400 MHz) 7.50 (d, J=1.8 Hz, 2H), 7.43 (t, J=1.8Hz, 1H), 7.39 (d, J=8.6 Hz, 1H), 6.95-7.0 (m, 2H), 6.29 (t, J=7.0 Hz,1H), 5.68 (bs, 2H), 4.05-4.15 (m, 2H), 4.04 (d, J=17.2 Hz, 1H), 3.67 (d,J=17.2 Hz, 1H).

Synthetic Example 134-[5-(3,5-dichlorophenyl)-5-trifluoromethyl-4,5-dihydroisoxazol-3-yl]-2-methylthio-N-(2-pyridylmethyl)benzoicacid amide (Compound of the Present Invention No. 5-323)

In a solution of 0.92 g of4-[5-(3,5-dichlorophenyl)-5-trifluoromethyl-4,5-dihydroisoxazol-3-yl]-2-fluoro-N-(2-pyridylmethyl)benzoicacid amide (Compound of the present invention No. 5-041) synthesizedsimilarly to Synthetic Example 4 in 12 ml of dimethylsulfoxide, 0.12 gof sodium methane thiolate was added with stirring at room temperature,and stirred at 100° C. for 90 minutes. After the completion of thereaction, the reaction mixture was poured in 30 ml of water, andextracted with ethyl acetate (20 ml×3). The organic phase was washedwith 30 ml of water, dehydrated with saturated sodium chloride aqueoussolution and dried over anhydrous sodium sulfate, and then the solventwas distilled off under reduced pressure. The residue was purified withsilica gel column chromatography that was eluated with chloroform, and0.89 g of the aimed product was obtained as colorless oily substance.

¹H NMR (CDCl₃, Me₄Si, 300 MHz) 8.51 (d, J=4.8 Hz, 1H), 7.6-7.75 (m, 4H),7.52 (bs, 2H), 7.42 (bs, 1H), 7.37 (bs, 1H), 7.34 (bs, 1H), 7.20 (dd,J=6.9, 1.8 Hz, 1H), 4.74 (d, J=4.8 Hz, 2H), 4.10 (d, J=17.1 Hz, 1H),3.75 (d, J=17.1 Hz, 1H), 2.47 (s, 3H).

Synthetic Example 144-[5-(3,5-dichlorophenyl)-5-trifluoromethyl-4,5-dihydroisoxazol-3-yl]-2-methylsulfinyl-N-(2,2,2-trifluoroethyl)benzoicacid amide (Compound of the Present Invention No. 5-324)

In a solution of 0.38 g of4-[5-(3,5-dichlorophenyl)-5-trifluoromethyl-4,5-dihydroisoxazol-3-yl]-2-methylthio-N-(2,2,2-trifluoroethyl)benzoicacid amide (Compound of the present invention No. 5-322) synthesizedsimilarly to Synthetic Example 13 in 6 ml of 1,2-dichloroethane, 0.10 gof N-chlorosuccinic acid imide was added with stirring at roomtemperature, and stirred at the same temperature for 11 hours. After thecompletion of the reaction, the reaction mixture was poured in 30 ml ofwater, and extracted with ethyl acetate (20 ml×3). The organic phase waswashed with 30 ml of saturated sodium hydrogen carbonate, dehydratedwith saturated sodium chloride aqueous solution and dried over anhydroussodium sulfate, and then the solvent was distilled off under reducedpressure. The residue was purified with silica gel column chromatographythat was eluated with ethyl acetate-hexane (1:2), and 0.17 g of theaimed product was obtained as colorless oily substance.

¹H NMR (CDCl₃, Me₄Si, 300 MHz) 8.16 (t, J=8.1 Hz, 1H), 7.6-7.8 (m, 3H),7.55 (d, J=8.1 Hz, 1H), 7.51 (d, J=8.1 Hz, 1H), 7.15 and 7.11 (t, J=6.3Hz, 1H), 4.18 (qd, J=18.5, 6.3 Hz, 2H), 4.15 (d, J=17.7 Hz, 1H), 3.80(d, J=17.7 Hz, 1H), 2.79 and 2.78 (s, 3H).

Synthetic Example 154-[5-(3,5-dichlorophenyl)-5-trifluoromethyl-4,5-dihydroisoxazol-3-yl]-2-methylsulfonyl-N-(2,2,2-trifluoroethyl)benzoicacid amide (Compound of the Present Invention No. 5-326)

In a solution of 0.25 g of4-[5-(3,5-dichlorophenyl)-5-trifluoromethyl-4,5-dihydroisoxazol-3-yl]-2-methylthio-N-(2,2,2-trifluoroethyl)benzoicacid amide (Compound of the present invention No. 5-322) synthesizedsimilarly to Synthetic Example 13 in 6 ml of dichloromethane, 0.17 g of3-chloroperbenzoic acid was added with stirring at room temperature, andstirred at the same temperature for 3 days. After the completion of thereaction, the reaction mixture was poured in 30 ml of sodium thiosulfateaqueous solution, and extracted with chloroform (10 ml×3). The organicphase was dehydrated with saturated sodium chloride aqueous solution anddried over anhydrous sodium sulfate, and then the solvent was distilledoff under reduced pressure. The residue was purified with silica gelcolumn chromatography that was eluated with chloroform, and 0.20 g ofthe aimed product was obtained as colorless oily substance.

¹H NMR (CDCl₃, Me₄Si, 300 MHz) 8.16 (t, J=8.4 Hz, 1H), 8.05 (bs, 1H),8.00 (s, 1H), 7.92 (s, 1H), 7.55 (d, J=8.4 Hz, 1H), 7.52 (d, J=8.4 Hz,1H), 7.06 and 7.02 (t, J=6.4 Hz, 1H), 4.17 (d, J=17.4 Hz, 1H), 4.16 (qd,J=18.5, 6.3 Hz, 2H), 3.79 (d, J=17.4 Hz, 1H), 2.12 (s, 3H).

Synthetic Example 162-Cyano-4-[5-(3,5-dichlorophenyl)-5-trifluoromethyl-4,5-dihydroisoxazol-3-yl]-N-(2-pyridylmethyl)benzoicacid amide (Compound of the Present Invention No. 5-341)

In a solution of 0.19 g of4-[5-(3,5-dichlorophenyl)-5-trifluoromethyl-4,5-dihydroisoxazol-3-yl]-2-iodo-N-(2-pyridylmethyl)benzoicacid amide (Compound of the present invention No. 5-065) synthesizedsimilarly to Synthetic Example 4 in 10 ml of dimethylacetamide, 36.0 mgof zinc cyanide, 4.8 mg of zinc, 11.0 mg of tris(dibenzylideneacetone)dipalladium and 13.5 mg of 1,1′-bis(diphenylphosphino)ferrocene wereadded, and stirred under nitrogen atmosphere at 80 to 120° C. for 5hours. After the completion of the reaction, 30 ml of ammonia water and20 ml of water were added in the reaction mixture, and extracted withethyl acetate (50 ml×1). The organic phase was washed with 30 ml ofwater, dehydrated with saturated sodium chloride aqueous solution anddried over anhydrous sodium sulfate, and then the solvent was distilledoff under reduced pressure. The residue was purified with silica gelcolumn chromatography that was eluated with ethylacetate-hexane (2:1),and 0.05 g of the aimed product was obtained as brown resinoussubstance.

¹H NMR (CDCl₃, Me₄Si, 400 MHz) 8.5-8.6 (m, 1H), 8.12 (bs, 1H), 7.9-8.0(m, 2H), 7.15-7.7 (m, 7H), 5.13 (bs, 2H), 4.14 (d, J=17.4 Hz, 1H), 3.78(d, J=17.4 Hz, 1H).

Synthetic Example 172-Acetylamino-4-[5-(3,5-dichlorophenyl)-5-trifluoromethyl-4,5-dihydroisoxazol-3-yl]-N-(2,2,2-trifluoroethyl)benzoicacid amide (Compound of the Present Invention No. 5-333)

In a solution of 0.05 g of2-amino-4-[5-(3,5-dichlorophenyl)-5-trifluoromethyl-4,5-dihydroisoxazol-3-yl]-N-(2,2,2-trifluoroethyl)benzoicacid amide (Compound of the present invention No. 5-329) synthesized inSynthetic Example 12 and 0.15 ml of triethylamine in 2 ml of chloroform,0.10 ml of acetic anhydride was added under cooling with ice withstirring, and stirred at room temperature for 20 hours. After thecompletion of the reaction, the reaction mixture was subjected topurification with medium-pressure preparative liquid chromatography(Yamazen Corporation, medium pressure preparative system; YFLC-Wprep)that was eluted with ethyl acetate-hexane (1:8 to 1:1 gradient), and0.045 g of the aimed product was obtained as pale yellow resinoussubstance.

¹H NMR (CDCl₃, Me₄Si, 400 MHz) 10.90 (bs, 1H), 8.77 (d, J=1.3 Hz, 1H),7.57 (dd, J=8.4, 1.5 Hz, 1H), 7.53 (d, J=8.4 Hz, 1H), 7.50 (d, J=1.7 Hz,2H), 7.45 (t, J=1.8 Hz, 1H), 6.82 (bs, 1H), 4.1-4.2 (m, 2H), 4.11 (d,J=17.0 Hz, 1H), 3.73 (d, J=17.0 Hz, 1H), 2.22 (s, 3H).

Synthetic Example 184-[5-(3,5-Dichlorophenyl)-5-trifluoromethyl-4,5-dihydroisoxazol-3-yl]-2-methylamino-N-(2,2,2-trifluoroethyl)benzoicacid amide (Compound of the Present Invention No. 5-331) and4-[5-(3,5-dichlorophenyl)-5-trifluoromethyl-4,5-dihydroisoxazol-3-yl]-2-dimethylamino-N-(2,2,2-trifluoroethyl)benzoicacid amide (Compound of the Present Invention No. 5-334)

In a solution of 0.25 g of2-amino-4-[5-(3,5-dichlorophenyl)-5-trifluoromethyl-4,5-dihydroisoxazol-3-yl]-N-(2,2,2-trifluoroethyl)benzoicacid amide (Compound of the present invention No. 5-329) synthesized inSynthetic Example 12 and 0.06 g of 36% formaldehyde aqueous solution in7 ml of 1,2-dichloroethane, 1.00 g of sodium triacetoxy borohydride wasadded with stirring at room temperature in three portions at 1hour-interval, and continued to stir at the same temperature for further2 hours. After the completion of the reaction, the reaction mixture waspoured to 5 ml of ice water, the organic phase was collected, and thesolvent was distilled under reduced pressure. The residue was subjectedto purification with medium-pressure preparative liquid chromatography(Yamazen Corporation, medium pressure preparative system; YFLC-Wprep)that was eluted with ethyl acetate-hexane (0:1 to 1:3 gradient), and0.13 g of4-[5-(3,5-dichlorophenyl)-5-trifluoromethyl-4,5-dihydroisoxazol-3-yl]-2-methylamino-N-(2,2,2-trifluoroethyl)benzoicacid amide was obtained as pale yellow crystal, and 0.13 g of4-[5-(3,5-dichlorophenyl)-5-trifluoromethyl-4,5-dihydroisoxazol-3-yl]-2-dimethylamino-N-(2,2,2-trifluoroethyl)benzoicacid amide was obtained as pale yellow resinous substance.4-[5-(3,5-dichlorophenyl)-5-trifluoromethyl-4,5-dihydroisoxazol-3-yl]-2-methylamino-N-(2,2,2-trifluoroethyl)benzoicacid amide;

Melting point 156.0 to 158.0° C.

¹H NMR (CDCl₃, Me₄Si, 400 MHz) 7.57 (bs, 1H), 7.52 (d, J=1.6 Hz, 2H),7.43 (t, J=1.8 Hz, 1H), 7.38 (d, J=8.2 Hz, 1H), 6.92 (d, J=1.6 Hz, 1H),6.84 (dd, J=8.2, 1.6 Hz, 1H), 6.31 (t, J=6.4 Hz, 1H), 4.0-4.15 (m, 2H),4.08 (d, J=17.2 Hz, 1H), 3.70 (d, J=17.2 Hz, 1H), 2.91 (s, 3H).

4-[5-(3,5-dichlorophenyl)-5-trifluoromethyl-4,5-dihydroisoxazol-3-yl]-2-dimethylamino—N-(2,2,2-trifluoroethyl)benzoic acid amide

¹H NMR (CDCl₃, Me₄Si, 400 MHz) 10.29 (t, J=6.2 Hz, 1H), 8.22 (d, J=8.1Hz, 1H), 7.73 (d, J=1.7 Hz, 1H), 7.52 (d, J=1.7 Hz, 2H), 7.44 (t, J=1.8Hz, 1H), 7.33 (dd, J=8.1, 1.6 Hz, 1H), 4.13 (qd, J=9.2, 6.2 Hz, 2H),4.10 (d, J=17.2 Hz, 1H), 3.72 (d, J=17.2 Hz, 1H), 2.78 (s, 6H).

Synthetic Example 194-[5-(3,5-Dichlorophenyl)-5-trifluoromethyl-4,5-dihydroisoxazol-3-yl]-N-(2-methoxyiminoethyl)-2-methylbenzoic acid amide (Compound of the Present Invention No. 5-113)

In a solution of 152 mg of4-[5-(3,5-dichlorophenyl)-5-trifluoromethyl-4,5-dihydroisoxazol-3-yl]-N-(2,2-dimethoxyethyl)-2-methylbenzoic acid amide (Compound of the present invention No. 5-083)synthesized similarly to Synthetic Example 5 in 14 ml of methanol-water(6:1) mixed solvent, 38 mg of methoxyamine hydrochloride was added, andstirred under reflux with heat for 8 hours. After the completion of thereaction, the reaction mixture was left and cooled to room temperature,diluted by adding 80 ml of ethyl acetate, washed with water (30 ml×2),and dehydrated with saturated sodium chloride aqueous solution and driedover anhydrous sodium sulfate, and then the solvent was distilled offunder reduced pressure. The residue was purified with silica gel columnchromatography that was eluated with ethylacetate-hexane (1:1), and 102mg of the aimed product was obtained as colorless resinous substance.

¹H NMR (CDCl₃, Me₄Si, 300 MHz) 7.45-7.55 (m, 6H), 7.45-7.55 and 6.83 (t,J=4.5 Hz, 1H), 7.4-7.45 (m, 1H), 6.28 and 6.16 (t, J=4.7 Hz, 1H), 4.27and 4.22 (t, J=4.7 Hz, 2H), 4.08 (d, J=17.1 Hz, 1H), 3.92 and 3.85 (s,3H), 3.70 (d, J=17.4 Hz, 1H), 2.50 and 2.48 (s, 3H).

Synthetic Example 20N-[4-[5-(3,5-Dichlorophenyl)-5-trifluoromethyl-4,5-dihydroisoxazol-3-yl]-2-methylbenzoyl]glycine(Compound of the Present Invention No. 5-127)

In a solution of 2.6 g of methylN-[4-[5-(3,5-dichlorophenyl)-5-trifluoromethyl-4,5-dihydroisoxazol-3-yl]-2-methylbenzoyl]glycine(Compound of the present invention No. 5-128) synthesized similarly toSynthetic Example 5 in 10 ml of methanol, a solution of 1.0 g ofpotassium hydroxide in 10 ml of water was added with stirring at roomtemperature, and stirred at the same temperature for further 1 hour.After the completion of the reaction, 10 ml of 12N hydrochloric acid wasadded and extracted with ethyl acetate (50 ml×1), the organic phase wasdehydrated with saturated sodium chloride aqueous solution and driedover anhydrous sodium sulfate, and then the solvent was distilled offunder reduced pressure to obtain 2.4 g of the aimed product as paleyellow resinous resinous substance.

¹H NMR (CDCl₃, Me₄Si, 300 MHz) 7.4-7.55 (m, 6H), 6.35-6.85 (m, 2H), 4.23(d, J=5.7 Hz, 2H), 4.08 (d, J=17.1 Hz, 1H), 3.71 (d, J=17.1 Hz, 1H),2.44 (s, 3H).

Synthetic Example 214-[5-(3,5-Dichlorophenyl)-5-trifluoromethyl-4,5-dihydroisoxazol-3-yl]-2-methyl-N—[N-(2,2,2-trifluoroethyl)carbamoylmethyl]benzoicacid amide (Compound of the Present Invention No. 5-151)

In a solution of 1.00 g ofN-[4-[5-(3,5-dichlorophenyl)-5-trifluoromethyl-4,5-dihydroisoxazol-3-yl]-2-methylbenzoyl]glycine(Compound of the present invention No. 5-127) synthesized in SyntheticExample 20 in 30 ml of dichloromethane, 0.65 g of1-[3-(diethylamino)propyl]-3-ethylcarbodiimide hydrochloride was added,and stirred at room temperature for 15 minutes, then 0.40 g of2,2,2-trifluoroethylamine and 0.40 g of 4-(N,N-dimethylamino)pyridinewere added and stirred at the same temperature for further 2 hours.After the completion of the reaction, the solvent was distilled offunder reduced pressure, the residue was purified with silica gel columnchromatography that was eluated with ethyl acetate-hexane (1:3), andthen crystallized from hexane to obtain 0.48 g of the aimed product aswhite crystal. Melting point 173.5 to 175.5° C.

¹H NMR (CDCl₃, Me₄Si, 300 MHz) 7.35-7.55 (m, 7H), 7.03 (t, J=5.1 Hz,1H), 4.21 (d, J=5.1 Hz, 2H), 4.09 (d, J=17.4 Hz, 1H), 3.85-4.0 (m, 2H),3.71 (d, J=17.4 Hz, 1H), 2.43 (s, 3H).

Synthetic Example 224-[5-(3,5-Dichlorophenyl)-5-trifluoromethyl-4,5-dihydroisoxazol-3-yl]-2-methyl-N-(N-phenylcarbamoylmethyl)benzoicacid amide (Compound of the Present Invention No. 5-169)

In a solution of 0.40 g ofN-[4-[5-(3,5-dichlorophenyl)-5-trifluoromethyl-4,5-dihydroisoxazol-3-yl]-2-methylbenzoyl]glycine(Compound of the present invention No. 5-127) synthesized in SyntheticExample 20 and 0.08 g of pyridine in 10 ml of dichloromethane, 0.12 g ofpivaloyl chloride was added, and stirred at room temperature for 2hours, then 0.50 g of aniline and 3 ml of triethylamine were added andstirred at the same temperature for further 1 hour. After the completionof the reaction, 20 ml of water was added in the reaction mixture andextracted with ethyl acetate (50 ml×1), the organic phase was dehydratedwith saturated sodium chloride aqueous solution and dried over anhydroussodium sulfate, and then the solvent was distilled off under reducedpressure. The residue was purified with silica gel column chromatographythat was eluated with ethyl acetate-hexane (2:1) to obtain 0.12 g of theaimed product as white crystal.

Melting point 181.0 to 183.0° C.

¹H NMR (CDCl₃, Me₄Si, 300 MHz) 8.54 (bs, 1H), 7.5-7.55 (m, 7H), 7.44 (t,J=2.0 Hz, 1H), 7.31 (t, J=8.0 Hz, 2H), 7.1-7.2 (m, 1H), 6.95 (bs, 1H),4.34 (d, J=5.0 Hz, 2H), 4.19 (d, J=17.2 Hz, 1H), 3.70 (d, J=17.2 Hz,1H), 2.49 (s, 3H).

Synthetic Example 234-[5-(3,5-Dichlorophenyl)-5-trifluoromethyl-4,5-dihydroisoxazol-3-yl]-2-methyl-N-methyl-N-(2-pyridylmethyl)benzoicacid amide (Compound of the Present Invention No. 6-020)

In a solution of 0.35 g of4-[5-(3,5-dichlorophenyl)-5-trifluoromethyl-4,5-dihydroisoxazol-3-yl]-2-methyl-N-(2-pyridylmethyl)benzoicacid amide (Compound of the present invention No. 5-234) synthesizedsimilarly to Synthetic Example 5 in 20 ml of N,N-dimethylformamide, 0.04g of 55% oily sodium hydride was added under cooling with ice withstirring, and stirred at the same temperature for 30 minutes. Then, 0.12g of methyl iodide was added and thereafter the temperature was raisedto room temperature, and continued to stir at the same temperature forfurther 2 hours. After the completion of the reaction, the reactionmixture was diluted with 80 ml of ethyl acetate, washed with water (50ml×2), dehydrated with saturated sodium chloride aqueous solution anddried over anhydrous magnesium sulfate, and then the solvent wasdistilled off under reduced pressure. The residue was purified with highperformance liquid chromatography that was eluated withacetonitrile-water (85:15) to obtain 0.25 g of the aimed product ascolorless resinous substance.

¹H NMR (CDCl₃, Me₄Si, 300 MHz) 8.5-8.6 (m, 1H), 7.6-7.75 (m, 1H),7.05-7.55 (m, 8H), 4.43 and 4.89 (bs, 2H), 4.06 and 4.09 (d, J=17.4 and17.1 Hz, 1H), 3.68 and 3.71 (d, J=17.4 and 17.1 Hz, 1H), 2.85 and 3.13(s, 3H), 2.35 and 2.38 (s, 3H).

Synthetic Example 247-[5-(3,5-Dichlorophenyl)-5-trifluoromethyl-4,5-dihydroisoxazol-3-yl]-1-methyl-3-(2-pyridylmethyl)-1,2,3,4-tetrahydroquinazolin-4-one(Compound of the Present Invention No. 6-071)

In a solution of 0.06 g of4-[5-(3,5-dichlorophenyl)-5-trifluoromethyl-4,5-dihydroisoxazol-3-yl]-2-methylamino-N-(2-pyridylmethyl)benzoicacid amide (Compound of the present invention No. 5-332) synthesizedsimilarly to Synthetic Example 18 in 5 ml of dichloromethane, 0.03 g ofchloromethylether was added, and stirred at the same temperature for 15hours After the completion of the reaction, the solvent was distilledoff under reduced pressure, and the residue was purified with silica gelcolumn chromatography that was eluated with ethyl acetate-hexane (3:1)to obtain 0.04 g of the aimed product as colorless oily substance.

¹H NMR (CDCl₃, Me₄Si, 300 MHz) 8.5-8.6 (m, 1H), 8.04 (d, J=7.8 Hz, 1H),7.6-7.75 (m, 1H), 7.4-7.55 (m, 4H), 7.15-7.3 (m, 1H), 7.10 (bs, 1H),6.95-7.05 (m, 1H), 4.86 (s, 2H), 4.06 (s, 2H), 4.09 (d, J=17.4 Hz, 1H),3.70 (d, J=17.4 Hz, 1H), 2.90 (s, 3H).

Synthetic Example 254-[5-(3,5-Dichlorophenyl)-5-trifluoromethyl-4,5-dihydroisoxazol-3-yl]-2-methyl-N-(2,2,2-trifluoroethyl)benzoicacid thioamide (Compound of the Present Invention No. 7-007)

A solution of 0.50 g of4-[5-(3,5-dichlorophenyl)-5-trifluoromethyl-4,5-dihydroisoxazol-3-yl]-2-methyl-N-(2,2,2-trifluoroethyl)benzoicacid amide (Compound of the present invention No. 5-075) synthesized inSynthetic Example 8 and 0.41 g of Lawesson's Reagent(2,4-bis(4-methoxyphenyl)-1,3,2,4-dithiadiphosphetan-2,4-disulfide) in15 ml of toluene was stirred under reflux with heat for 20 hours. Afterthe completion of the reaction, the reaction mixture was left and cooledto room temperature, and the reaction mixture was diluted with 60 ml ofethyl acetate, washed with water (50 ml×1), then dehydrated withsaturated sodium chloride aqueous solution and dried over anhydrousmagnesium sulfate, and then the solvent was distilled off under reducedpressure. The residue was purified with silica gel column chromatographythat was eluated with ethyl acetate-hexane (3:1) to obtain 0.40 g of theaimed product as yellow resinous substance.

¹H NMR (CDCl₃, Me₄Si, 300 MHz) 7.2-7.5 (m, 7H), 4.55-4.7 (m, 2H), 4.06(d, J=17.1 Hz, 1H), 3.68 (d, J=17.1 Hz, 1H), 2.38 (s, 3H).

Synthetic Example 264-[5-(3-Bromodifluoromethoxyphenyl)-5-trifluoromethyl-4,5-dihydroisoxazol-3-yl]-2-methyl-N-(2,2,2-trifluoroethyl)benzoicacid amide (Compound of the Present Invention No. 5-014) Step 1:Production of 3-bromodifluoromethoxy-1-iodobenzene

In a suspension of 0.87 g of 55% oily sodium hydride in 20 ml ofN,N-dimethylformamide, a solution of 4.00 g of 3-iodophenol in 10 ml ofN,N-dimethylformamide was added dropwise with stirring under icecooling, after the completion of the addition dropwise, stirred at roomtemperature for 30 minutes. The reaction mixture was added dropwise in asolution of 11.40 g of dibromodifluoromethane in 20 ml ofN,N-dimethylformamide under cooling with ice with stirring, after thecompletion of the addition dropwise, continued to stir at roomtemperature for 2 hours. After the completion of the reaction, 50 ml ofwater was added in the reaction mixture, extracted with ethyl acetate(100 ml×1), the organic phase was washed with water, then dehydratedwith saturated sodium chloride aqueous solution and dried over anhydrousmagnesium sulfate, and then the solvent was distilled off under reducedpressure. The residue was purified with silica gel column chromatographythat was eluated with hexane to obtain 2.10 g of the aimed product ascolorless oily substance.

¹H NMR (CDCl₃, Me₄Si, 300 MHz) 7.65-7.7 (m, 1H), 7.55-7.65 (m, 1H),7.2-7.3 (m, 1H), 7.15 (t, J=9.0 Hz, 1H).

Step 2: Production of3-bromodifluoromethoxy-1-(1-trifluoromethylethenyl)benzene

In 10 ml of a solution of 1-trifluoromethylethenyl zinc bromide preparedaccording to the method described in documents in 1M tetrahydrofuran,1.0 g of 3-bromodifluoromethoxy-1-iodobenzene and 0.05 g ofdichlorobis(triphenylphosphine) palladium (II) were added, and stirredunder reflux with heat for 2 hours. After the completion of thereaction, the reaction mixture was poured in 20 ml of dilutedhydrochloric acid, extracted with ethyl acetate (50 ml×1). The organicphase was dehydrated with saturated sodium chloride aqueous solution anddried over anhydrous sodium sulfate, and then the solvent was distilledoff under reduced pressure. The residue was dissolved in hexane, andhigh polar impurities were excluded by treating with silica gel toobtain 0.77 g of crude aimed product as colorless oily substance. Theresulting product was used as such without purification for the nextstep.

Step 3: Production of4-[5-(3-bromodifluoromethoxyphenyl)5-trifluoromethyl-4,5-dihydroisoxazol-3-yl]-2-methyl-N-(2,2,2-trifluoroethyl)benzoic acid amide

In a solution of 0.3 g of4-chlorohydroxyiminomethyl-2-methyl-N-(2,2,2-trifluoroethyl)benzoic acidamide synthesized similarly to Steps 1 to 3 of Synthetic Example 7 and0.2 g of crude3-bromodifluoromethoxy-1-(1-trifluoromethylethenyl)benzene in 10 ml of1,2-dimethoxyethane, 0.4 g of potassium hydrogen carbonate was added,and stirred at room temperature for 18 hours. After the completion ofthe reaction, the reaction mixture was poured in 20 ml of water,extracted with ethyl acetate (50 ml×1). The organic phase was dehydratedwith saturated sodium chloride aqueous solution and dried over anhydroussodium sulfate, and then the solvent was distilled off under reducedpressure. The residue was purified with silica gel column chromatographythat was eluated with ethyl acetate-hexane (1:1) to obtain 0.29 g of theaimed product as colorless glass substance.

¹H NMR (CDCl₃, Me₄Si, 400 MHz) 7.5-7.6 (m, 5H), 7.41 (d, J=7.8 Hz, 1H),7.3-7.5 (m, 1H), 6.16 (t, J=6.6 Hz, 1H), 4.05-4.15 (m, 3H), 3.74 (d,J=17.2 Hz, 1H), 2.45 (s, 3H).

Synthetic Example 274-[5-Chlorodifluoromethyl-5-(3,5-dichlorophenyl)-4,5-dihydroisoxazol-3-yl]-2-methyl-N-(2,2,2-trifluoroethyl)benzoicacid amide (Compound of the Present Invention No. 5-355) Step 1:Production of 2,3′,5′-trichloro-2,2-difluoroacetophenone

In a solution of 5.0 g of 3,5-dichloro-1-iodobenzene in 50 ml oft-butylmethylether, 12.2 ml of n-butyl lithium (1.58M hexane solution)was added dropwise at −78° C. with stirring, after the completion of theaddition dropwise, stirred at the same temperature for 30 minutes. 6.6 gof chlorodifluoroacetic acid methyl ester was added dropwise at −78° C.with stirring in the reaction mixture, after the completion of theaddition dropwise, continued to stir at 0° C. for further 30 minutes.After the completion of the reaction, the reaction mixture was poured in100 ml of saturated ammonium chloride aqueous solution, extracted withethyl acetate (100 ml×1). The organic phase was dehydrated withsaturated sodium chloride aqueous solution and dried over anhydrousmagnesium sulfate, and then the solvent was distilled off under reducedpressure to obtain 4.6 g of crude aimed product as pale yellow oilysubstance. The resulting product was used as such without purificationfor the next step.

¹H NMR (CDCl₃, Me₄Si, 300 MHz) 7.97 (s, 2H), 7.68 (s, 1H).

Step 2: Production of3,5-dichloro-1-[1-(chlorodifluorofluoromethyl)ethenyl]benzene

in a solution of 2.89 g of methyltriphenylphosphonium bromide in 15 mlof tetrahydrofuran, 0.91 g of potassium t-butoxide was added, andstirred at room temperature for 1 hour. Then, a solution of 2.00 g of2,3′,5′-trichloro-2,2-difluoroacetophenone in 5 ml of tetrahydrofuranwas added dropwise in the reaction mixture under cooling with ice withstirring, after the completion of the addition dropwise, continued tostir at room temperature for 1 hour. After the completion of thereaction, the reaction mixture was poured in 50 ml of ice water,extracted with ethyl acetate (50 ml×1), the organic phase was dehydratedwith saturated sodium chloride aqueous solution and dried over anhydroussodium sulfate, and then the solvent was distilled off under reducedpressure. The residue was purified with silica gel column chromatographythat was eluated with hexane to obtain 1.50 g of the aimed product asyellow oily substance.

¹H NMR (CDCl₃, Me₄Si, 300 MHz) 7.40 (s, 1H), 7.35 (s, 2H), 5.99 (s, 1H),5.65 (s, 1H).

Step 3: Production of4-[5-chlorodifluoromethyl-5-(3,5-dichlorophenyl)-4,5-dihydroisoxazol-3-yl]-2-methyl-N-(2,2,2-trifluoroethyl)benzoicacid amide

In a solution of 0.25 g of4-chlorohydroxyiminomethyl-2-methyl-N-(2,2,2-trifluoroethyl)benzoic acidamide synthesized similarly to Steps 1 to 3 of Synthetic Example 7 and0.26 g of 3,5-dichloro-1-[1-(chlorodifluorofluoromethyl)ethenyl]benzenein 3 ml of 1,2-dimethoxyethane, 0.43 g of potassium hydrogen carbonateand a small amount of water were added, and stirred at room temperaturefor 15 hours. After the completion of the reaction, the reaction mixturewas filtered and thereby solid substance was excluded, and the filtratewas concentrated under reduced pressure. The residue was purified withsilica gel column chromatography that was eluated with ethylacetate-hexane (2:3) to obtain 0.28 g of the aimed product as yellowoily substance.

¹H NMR (CDCl₃, Me₄Si, 300 MHz) 7.35-7.65 (m, 6H), 6.06 (t, J=6.1 Hz,1H), 4.0-4.25 (m, 3H), 3.72 (d, J=17.1 Hz, 1H), 2.47 (s, 3H).

Synthetic Example 284-[5-(3,5-Dichlorophenyl)-5-trifluoromethyl-4,5-dihydroisoxazol-3-yl]-2-methyl-N-methoxycarbonyl-N-(2-pyridylmethyl)benzoicacid amide (Compound of the Present Invention No. 6-043) Step 1:Production of5-(3,5-dichlorophenyl)-3-(3-methyl-4-nitrophenyl)-5-trifluoromethyl-4,5-dihydroisoxazole

In a solution of 1.31 g of3,5-dichloro-1-(1-trifluoromethylethenyl)benzene synthesized in Step 1of Synthetic Example 3 and 1.17 g of

-chloro-3-methyl-4-nitrobenzaldoxime in 10 ml of tetrahydrofuran, 1.15 gof potassium hydrogen carbonate and 1.50 g of water were added, andstirred at room temperature for 18 hours. After the completion of thereaction, tetrahydrofuran was removed from the reaction mixture, 3 ml ofwater was added, and stirred under colloing with ice for further 30minutes. Precipitated crystal was filtered off, washed with 5 ml ofwater and then 5 ml of diisopropyl ether to obtain 1.29 g of the aimedproduct as white crystal.

Melting point 135.0 to 136.0° C.

¹H NMR (CDCl₃, Me₄Si, 300 MHz) 8.03 (d, J=7.5 Hz, 1H), 7.6-7.75 (m, 2H),7.51 (bs, 2H), 7.44 (t, J=1.8 Hz, 1H), 4.11 (d, J=17.4 Hz, 1H), 3.73 (d,J=17.4 Hz, 1H), 2.64 (s, 3H).

Step 2: Production of3-(4-amino-3-methylphenyl)-5-(3,5-dichlorophenyl)-5-trifluoromethyl-4,5-dihydroisoxazole

In a solution of 1.23 g of5-(3,5-dichlorophenyl)-3-(3-methyl-4-nitrophenyl)-5-trifluoromethyl-4,5-dihydroisoxazolein 10 ml of ethyl acetate, 5.0 ml of water, 5.0 ml of acetic acid and0.66 g of reduced iron were added and stirred at 100° C. for 2 hours.After the completion of the reaction, the reaction mixture was filteredthrough Celite, 20 ml of water was added in the filtrate, extracted withethyl acetate (20 ml×2). The organic phases together were washed with 10ml of saturated sodium hydrogen carbonate aqueous solution, and thenwith 10 ml of water, thereafter dehydrated with saturated sodiumchloride aqueous solution and dried over anhydrous sodium sulfate, andthen the solvent was distilled off under reduced pressure to obtain 1.05g of crude aimed product as red-brown oily substance. The resultingproduct was used as such without purification for the next step.

¹H NMR (CDCl₃, Me₄Si, 300 MHz) 7.52 (s, 2H), 7.35-7.5 (m, 2H), 7.31 (dd,J=8.0, 2.0 Hz, 1H), 6.65 (d, J=8.4 Hz, 1H), 4.05 (d, J=17.1 Hz, 1H),3.93 (bs, 2H), 3.64 (d, J=17.1 Hz, 1H), 2.17 (s, 3H).

Step 3: Production of3-(4-bromo-3-methylphenyl)-5-(3,5-dichlorophenyl)-5-trifluoromethyl-4,5-dihydroisoxazole

in a solution of 0.50 g of3-(4-amino-3-methylphenyl)-5-(3,5-dichlorophenyl)-5-trifluoromethyl-4,5-dihydroisoxazolein 1.0 ml of 1,4-dioxane and 2.0 ml of water, 1.0 ml of 47% hydrobromicacid was added, and stirred under reflux with heat for 1 hour. Then, thereaction mixture was cooled with ice, and a solution of 0.10 g of sodiumnitrite in 1.0 ml of water was slowly added dropwise with stirring at atemperature of 5° C. or less, after the completion of the additiondropwise, continued to stir at the same temperature for further 1 hour.The diazo mixture was slowly added dropwise in a mixture of 1.0 ml of47% hydrobromic acid and 0.28 g of copper (I) bromide at 60° C. withstirring, after the completion of the addition dropwise, continued tostir at 60° C. for further 2 hours. After the completion of thereaction, 10 ml of water was added in the reaction mixture, extractedwith ethyl acetate (20 ml×2), the organic phases together were washedwith water, then dehydrated with saturated sodium chloride aqueoussolution and dried over anhydrous sodium sulfate, and then the solventwas distilled off under reduced pressure. The residue was purified withsilica gel column chromatography that was eluated with ethylacetate-hexane (1:10) to obtain 0.43 g of the aimed product as paleyellow crystal.

Melting point 105.0 to 108.0° C.

¹H NMR (CDCl₃, Me₄Si, 300 MHz) 7.59 (d, J=8.4 Hz, 1H), 7.45-7.55 (m,3H), 7.42 (t, J=1.8 Hz, 1H), 7.33 (dd, J=8.4, 2.1 Hz, 1H), 4.07 (d,J=17.1 Hz, 1H), 3.68 (d, J=17.1 Hz, 1H), 2.43 (s, 3H).

Step 4: Production of4-[5-(3,5-dichlorophenyl)-5-trifluoromethyl-4,5-dihydroisoxazol-3-yl]-2-methylbenzoicacid ethyl ester

In a solution of 15.0 g of3-(4-bromo-3-methylphenyl)-5-(3,5-dichlorophenyl)-5-trifluoromethyl-4,5-dihydroisoxazolein 60 ml of ethanol in an autoclave, 3.26 g of sodium acetate, 0.37 g of1,1′-bis(diphenylphosphino) ferrocene and 0.08 g of palladium (II)acetate were added, and stirred under 2.0 MPa carbon monoxide atmosphereat 110° C. for 3 hours. After the completion of the reaction, thereaction mixture was left and cooled to room temperature, 200 ml ofwater was added and extracted with ethyl acetate (200 ml×2), the organicphase was washed with water, dehydrated with saturated sodium chlorideaqueous solution and dried over anhydrous sodium sulfate and the solventwas distilled off under reduced pressure. The residue was purified withsilica gel column chromatography that was eluted with ethylacetate-hexane (1:8) to obtain 10.8 g of the aimed product as colorlessclear liquid. Refractive index n_(D) ^(21.4° C.)=1.5474

¹H NMR (CDCl₃, Me₄Si, 300 MHz) 7.95 (d, J=8.4 Hz, 1H), 7.45-7.65 (m,4H), 7.43 (t, J=1.8 Hz, 1H), 4.37 (q, J=7.2 Hz, 2H), 4.10 (d, J=17.4 Hz,1H), 3.71 (d, J=17.1 Hz, 1H), 2.62 (s, 3H), 1.40 (t, J=7.2 Hz, 3H).

Step 5: Production of4-[5-(3,5-dichlorophenyl)-5-trifluoromethyl-4,5-dihydroisoxazol-3-yl]-2-methylbenzoic acid

In a solution of 10.79 g of4-[5-(3,5-dichlorophenyl)-5-trifluoromethyl-4,5-dihydroisoxazol-3-yl]-2-methylbenzoicacid ethyl ester in 50 ml of ethanol and 10 ml of water, a solution of2.0 g of sodium hydroxide in 10 ml of water was slowly added withstirring at room temperature. Then, the reaction mixture was stirred at80° C. for 2 hours, after the completion of the reaction, ethanol wasdistilled off under reduced pressure. The residue was adjusted to pH 1-2with concentrated hydrochloric acid with stirring at 50° C., thencontinued to stir at the same temperature for 1 hour and then at 5° C.for 1 hour. Precipitated crystal was filtered off, washed with water anddried to obtain 9.36 g of the aimed product as white crystal.

Melting point 146.0 to 148.5° C.

¹H NMR (CDCl₃, Me₄Si, 300 MHz) 8.12 (d, J=8.7 Hz, 1H), 7.5-7.7 (m, 2H),7.52 (d, J=1.5 Hz, 2H), 7.43 (d, J=1.5 Hz, 1H), 4.11 (d, J=16.8 Hz, 1H),3.73 (d, J=17.4 Hz, 1H), 2.69 (s, 3H).

Step 6: Production of4-[5-(3,5-dichlorophenyl)-5-trifluoromethyl-4,5-dihydroisoxazol-3-yl]-2-methyl-N-methoxycarbonyl-N-(2-pyridylmethyl)benzoicacid amide

In a solution of 1.00 g of4-[5-(3,5-dichlorophenyl)-5-trifluoromethyl-4,5-dihydroisoxazol-3-yl]-2-methylbenzoic acid in 30 ml of toluene, 0.43 g of thionyl chloride and 3 dropsof N,N-dimethylformamide were added, and stirred at 90° C. for 1 hour.After the completion of the reaction, the solvent was distilled offunder reduced pressure, and the residue was dissolved in 5 ml oftetrahydrofuran. In a solution of 0.40 g of N-(2-pyridylmethyl)carbamicacid methyl ester in 5 ml of tetrahydrofuran, 0.27 g of t-butoxypotassium was added at room temperature with stirring, and stirred atthe same temperature for 3 minutes. Then, the above-mentioned solutionof acid chloride in tetrahydrofuran was added dropwise in the reactionmixture, after the completion of the addition dropwise, continued tostir at the same temperature for further 1 hour. After the completion ofthe reaction, the reaction mixture was diluted with 60 ml of ethylacetate, washed with 50 ml of water, then dehydrated with saturatedsodium chloride aqueous solution and dried over anhydrous sodium sulfateand the solvent was distilled off under reduced pressure. The residuewas purified with silica gel column chromatography that was eluted withethyl acetate-hexane (1:2 to 1:1) to obtain 0.75 g of the aimed productas yellow resinous substance.

¹H NMR (CDCl₃, Me₄Si, 300 MHz) 8.56 (d, J=4.8 Hz, 1H), 7.65-7.7 (m, 1H),7.5-7.55 (m, 4H), 7.35-7.45 (m, 2H), 7.15-7.3 (m, 2H), 5.21 (s, 2H),4.09 (d, J=17.4 Hz, 1H), 3.70 (d, J=17.4 Hz, 1H), 3.58 (s, 3H), 2.40 (s,3H).

Synthetic Example 294-[5-(3,5-Dichlorophenyl)-5-trifluoromethyl-4,5-dihydroisoxazol-3-yl]-2-methylbenzoicacid amide (Compound of the Present Invention No. 5-066) Step 1:Production of 4-bromo-chloro-3-methylbenzaldoxime

In a solution of 82.0 g of 4-bromo-3-methylbenzaldoxime in 450 ml oftetrahydrofuran, 120.0 g of concentrated hydrochloric acid was added adropwise with stirring under ice cooling over 45 minutes. Then, 220 mlof 8% sodium hypochlorite aqueous solution was carefully added dropwiseover 75 minutes so that the temperature of the reaction mixture wouldnot exceed 5° C., after the completion of the addition, continued tostir at 10° C. or less further for 90 minutes. After the completion ofthe reaction, nitrogen gas was blown through the reaction mixture for 45minutes and precipitated insoluble material was filtered off, andtetrahydrofuran was distilled off under reduced pressure. The remainingaqueous solution was extracted with 240.0 g of ethyl acetate. Theorganic phase was washed with water (240 ml×2) and then insolublematerial was filtered off, the solvent was distilled off under reducedpressure to obtain 93.5 g of the aimed product as pale yellow crystal.

Melting point 77.0 to 78.0° C.

¹H NMR (CDCl₃, Me₄Si, 400 MHz) 8.00 (bs, 1H), 7.71 (d, J=2.2 Hz, 1H),7.57 (d, J=8.4 Hz, 1H), 7.51 (dd, J=8.4, 2.2 Hz, 1H), 2.44 (s, 3H).

Step 2: Production of3-(4-bromo-3-methylphenyl)-5-(3,5-dichlorophenyl)-5-trifluoromethyl-4,5-dihydroisoxazole

In a solution of 22.7 g of3,5-dichloro-1-(1-trifluoromethylethenyl)benzene produced in Step 1 ofSynthetic Example 3 and 26.0 g of 4-bromo-chloro-3-methylbenzaldoxime in120 ml of tetrahydrofuran, 15.7 g of potassium hydrogen carbonate wasadded, and stirred under reflux with heat for 5 hours. After thecompletion of the reaction, the reaction mixture was left and cooled toroom temperature, insoluble material was filtered off, then the solventwas distilled off under reduced pressure. 150 ml of water was added inthe residue, stirred at room temperature for 18 hours, and precipitatedcrystal was filtered off and dried to obtain 38.6 g of the aimed productas white crystal. Melting point 105.0 to 108.0° C.

¹H NMR (CDCl₃, Me₄Si, 300 MHz) 7.59 (d, J=8.4 Hz, 1H), 7.45-7.55 (m,3H), 7.42 (t, J=1.8 Hz, 1H), 7.33 (dd, J=8.4, 2.1 Hz, 1H), 4.07 (d,J=17.1 Hz, 1H), 3.68 (d, J=17.1 Hz, 1H), 2.43 (s, 3H).

Step 3: Production of4-[5-(3,5-dichlorophenyl)-5-trifluoromethyl-4,5-dihydroisoxazol-3-yl]-2-methylbenzoylchloride

In a solution of 18.1 g of3-(4-bromo-3-methylphenyl)-5-(3,5-dichlorophenyl)-5-trifluoromethyl-4,5-dihydroisoxazoleand 3.94 g of sodium acetate in 42 ml of 1,2-dimethoxyethane and 42 mlof water in an autoclave, 0.42 g of triphenylphosphine and 0.09 g ofpalladium (II) acetate were added, and stirred under 1.5 MPa carbonmonoxide atmosphere at 110° C. for 7 hours. After the completion of thereaction, the reaction mixture was left and cooled to room temperature,the solid was filtered off, then added in 100 ml of ethyl acetate. Theorganic phase was washed with 1% sodium hydrogen carbonate aqueoussolution (70 ml×2), then with 1N hydrochloric acid (55 ml×2), dried withsaturated sodium chloride aqueous solution and then the solvent wasdisplaced by toluene. 2 drops of N,N-dimethylformamide was added in theresulting toluene solution, and 6.0 g of thionyl chloride was addeddropwise with stirring at 80° C., and continued to stir at the sametemperature further for 1.5 hour. After the completion of the reaction,insoluble material was filtered off, the solvent was distilled off underreduced pressure until the volume of the solvent was reduced to aboutone-third. Then, 50 ml of hexane was gradually added dropwise withstirring at 60° C., after the completion of the addition, left andcooled to room temperature with stirring, and continued to stir at roomtemperature further for 1 hour. Precipitated crystal was filtered offand dried to obtain 13.4 g of the aimed product as white crystal.

Melting point 140.5 to 143.0° C.

¹H NMR (CDCl₃, Me₄Si, 300 MHz) δ 8.25 (d, J=8.7 Hz, 1H), 7.64 (d, J=8.7Hz, 1H), 7.59 (s, 1H), 7.51 (s, 2H), 7.43 (s, 1H), 4.11 (d, J=17.4 Hz,1H), 3.73 (d, J=17.4 Hz, 1H), 2.60 (s, 3H).

Step 4: Production of4-[5-(3,5-dichlorophenyl)-5-trifluoromethyl-4,5-dihydroisoxazol-3-yl]-2-methylbenzoicacid amide

In a mixture of 3.0 g of concentrated ammonia water and 15 ml oftetrahydrofuran, a solution of 3.0 g of4-[5-(3,5-dichlorophenyl)-5-trifluoromethyl-4,5-dihydroisoxazol-3-yl]-2-methylbenzoylchloride in 20 ml of tetrahydrofuran was added dropwise, after thecompletion of the addition, continued to stir further for 18 hours.After the completion of the reaction, the solvent was distilled offunder reduced pressure, the residue was dissolved in 50 ml of ethylacetate, washed with 50 ml of water, dehydrated and dried with saturatedsodium chloride aqueous solution and anhydrous sodium sulfate in thatorder, and the solvent was distilled off under reduced pressure toobtain 2.9 g of the aimed product as orange crystal.

Melting point 162.5 to 164.0° C.

¹H NMR (CDCl₃, Me₄Si, 400 MHz) δ 7.45-7.55 (m, 6H), 6.40 (bs, 1H), 6.00(bs, 1H), 4.09 (d, J=17.0 Hz, 1H), 3.71 (d, J=17.0 Hz, 1H), 2.49 (s,3H).

Synthetic Example 304-[5-(3,5-Dichlorophenyl)-5-trifluoromethyl-4,5-dihydroisoxazol-3-yl]-2-methyl-N-(2,2,2-trifluoroethoxymethyl)benzoicacid amide (Compound of the Present Invention No. 5-480) Step 1:Production of4-[5-(3,5-dichlorophenyl)-5-trifluoromethyl-4,5-dihydroisoxazol-3-yl]-2-methyl-N-hydroxymethyl)benzoic acid amide

In a solution of 7.00 g of4-[5-(3,5-dichlorophenyl)-5-trifluoromethyl-4,5-dihydroisoxazol-3-yl]-2-methylbenzoicacid amide synthesized in Synthetic Example 29 in 70 ml of 1,4-dioxane,1.82 g of 37% formalin aqueous solution, 7.00 g of potassium carbonateand 15 ml of water were added, stirred at the same temperature for 3hours. After the completion of the reaction, the reaction mixture wasdiluted by adding 200 ml of ethyl acetate, washed with water (50 ml×1)and then dehydrated and dried with saturated sodium chloride aqueoussolution and anhydrous magnesium sulfate in that order, and filteredthrough silica gel, the solvent was distilled off under reduced pressureto obtain 7.00 g of crude aimed product as white crystal.

Melting point 69.0 to 73.0° C.

Step 2: Production of4-[5-(3,5-dichlorophenyl)-5-trifluoromethyl-4,5-dihydroisoxazol-3-yl]-2-methyl-N-(2,2,2-trifluoroethoxymethyl)benzoicacid amide

In a solution of 1.70 g of4-[5-(3,5-dichlorophenyl)-5-trifluoromethyl-4,5-dihydroisoxazol-3-yl]-2-methyl-N-(hydroxymethyl)benzoicacid amide in 20 ml of dichloromethane, 0.68 g of thionyl chloride wasadded with stirring at room temperature, stirred at the same temperaturefor 2 hours, then the solvent was distilled off under reduced pressure,and the residue was dissolved in 10 ml of tetrahydrofuran. In 0.33 g of60% oily sodium hydride suspended in 30 ml of tetrahydrofuran, 1.50 g of2,2,2-trifluoroethanol was added dropwise with stirring under icecooling, and stirred at the same temperature for 10 minutes. Then, thesolution of benzoic acid chloride in tetrahydrofuran prepared above wasadded dropwise in the reaction mixture with stirring under ice cooling,after the completion of the addition, continued to stir at roomtemperature for 1 hour. After the completion of the reaction, 50 ml ofwater was added in the reaction mixture, extracted with ethyl acetate(70 ml×1), and the organic phase was dehydrated and dried with saturatedsodium chloride aqueous solution and anhydrous magnesium sulfate in thatorder, and then the solvent was distilled off under reduced pressure.The residue was purified with silica gel column chromatography that waseluated with ethyl acetate-hexane (2:3) to obtain 1.20 g of the aimedproduct as colorless resinous substance.

¹H NMR (CDCl₃, Me₄Si, 400 MHz) δ 7.5-7.55 (m, 4H), 7.4-7.5 (m, 2H), 6.64(t, J=6.4 Hz, 1H), 5.02 (d, J=7.2 Hz, 2H), 4.05-4.15 (m, 3H), 3.70 (d,J=17.4 Hz, 1H), 2.49 (s, 3H).

Synthetic Example 31N-Carbamoylmethyl-4-[5-(3,5-dichlorophenyl)-5-trifluoromethyl-4,5-dihydroisoxazol-3-yl]-2-methylbenzoic acid amide (Compound of the Present Invention No. 5-137)

In a solution of 0.37 g of glycine amide hydrochloride and 0.71 g ofpyridine in 20 ml of dichloromethane, a solution of 1.31 g of4-[5-(3,5-dichlorophenyl)-5-trifluoromethyl-4,5-dihydroisoxazol-3-yl]-2-methylbenzoylchloride synthesized in Step 3 of Synthetic Example 29 in 10 ml ofdichloromethane was added dropwise with stirring under ice cooling,after the completion of the addition, stirred at room temperature for 3hours, then 3.00 g of triethyl amine was added in the reaction mixture,and continued to stir at the same temperature further for 30 minutes.After the completion of the reaction, the solvent was distilled offunder reduced pressure, 50 ml of ethyl acetate and 50 ml of water wereadded in the residue, and the organic phase was collected, and theaqueous phase was further extracted with ethyl acetate (50 ml×2). Theorganic phases together were dehydrated and dried with saturated sodiumchloride aqueous solution and anhydrous sodium sulfate in that order,and the solvent was distilled off under reduced pressure, the residualsolid was washed with hexane to obtain 1.24 g of the aimed product aswhite crystal.

Melting point 87.0 to 91.0° C.

¹H NMR (CDCl₃, Me₄Si, 300 MHz) δ 7.4-7.55 (m, 6H), 7.15-7.25 (m, 1H),6.86 (s, 1H), 5.88 (s, 1H), 4.12 (d, J=5.1 Hz, 2H), 4.11 (d, J=17.4 Hz,1H), 3.74 (d, J=17.4 Hz, 1H), 2.49 (s, 3H).

Synthetic Example 32N-Aminomethyl-4-[5-(3,5-dichlorophenyl)-5-trifluoromethyl-4,5-dihydroisoxazol-3-yl]-2-methylbenzoic acid amide hydrochloride (Compound of the Present Invention No.5-507)

In a solution of 0.47 g of [bis(trifluoroacetoxy)iodo]benzene in 12 mlof acetonitrile-water (1:1), a solution of 0.47 g ofN-carbamoylmethyl-4-[5-(3,5-dichlorophenyl)-5-trifluoromethyl-4,5-dihydroisoxazol-3-yl]-2-methylbenzoic acid amide synthesized in Synthetic Example 31 was added withstirring at room temperature, and stirred at room temperature for 5hours. After the completion of the reaction, 75 ml of water was added inthe reaction mixture, 8 ml of concentrated hydrochloric acid was added,then washed with 100 ml of diethyl ether, and the organic phase wassubjected to back extraction with 2N hydrochloric acid aqueous solution(20 ml×2). The aqueous phase was combined with the organic phase, waterwas distilled off, and the residual solid was washed with ethyl acetateto obtain 0.21 g of the aimed product as white crystal. Melting point155.0 to 157.0° C.

¹H NMR (CDCl₃, Me₄Si, 300 MHz) δ 9.0-9.1 (m, 1H), 7.4-7.7 (m, 8H), 4.64(d, J=5.7 Hz, 2H), 4.16 (d, J=17.4 Hz, 1H), 3.80 (d, J=17.4 Hz, 1H),2.50 (s, 3H).

Synthetic Example 33N-[4-[5-(3,5-Dichlorophenyl)-5-trifluoromethyl-4,5-dihydroisoxazol-3-yl]-2-methylbenzoylaminomethyl]carbamic acid methyl ester (Compound of the PresentInvention No. 5-515)

In a suspended solution of 0.13 g ofN-aminomethyl-4-[5-(3,5-dichlorophenyl)-5-trifluoromethyl-4,5-dihydroisoxazol-3-yl]-2-methylbenzoic acid amide hydrochloride synthesized in Synthetic Example 32 in4 ml of dichloromethane, 0.03 g of methyl chloroformate and 0.08 g oftriethyl amine were added with stirring at room temperature, and stirredat room temperature for 3 hours. After the completion of the reaction,the solvent was distilled under reduced pressure, the residue waspurified with silica gel column chromatography that was eluated withethyl acetate-hexane (1:1) to obtain 0.06 g of the aimed product ascolorless resinous substance.

¹H NMR (CDCl₃, Me₄Si, 300 MHz) δ 7.35-7.55 (m, 6H), 7.17 (bs, 1H), 6.12(bs, 1H), 4.73 (t, J=6.6 Hz, 2H), 4.09 (d, J=17.4 Hz, 1H), 3.71 (d,J=17.4 Hz, 1H), 3.68 (s, 3H), 2.42 (s, 3H).

Synthetic Example 34N-[4-[5-(3,5-Dichlorophenyl)-5-trifluoromethyl-4,5-dihydroisoxazol-3-yl]-2-methyl-N-(2-tetrahydrofuranyl)benzoicacid amide (Compound of the Present Invention No. 5-494)

In a solution of 1.25 g ofN-[4-[5-(3,5-dichlorophenyl)-5-trifluoromethyl-4,5-dihydroisoxazol-3-yl]-2-methylbenzoic acid amide synthesized in Synthetic Example 29 and 0.32 g of2,3-dihydrofuran in 30 ml of dichloromethane, 0.01 g of p-toluenesulfonic acid monohydrate was added with stirring at room temperature,and stirred at room temperature for 3 days. After the completion of thereaction, 30 ml of saturated sodium hydrogen carbonate aqueous solutionwas added in the reaction mixture, and extracted with ethyl acetate (30ml×2), the organic phase was dehydrated and dried with saturated sodiumchloride aqueous solution and anhydrous sodium sulfate in that order,and the solvent was distilled under reduced pressure. The residue waspurified with silica gel column chromatography that was eluated withethyl acetate-hexane (1:1) to obtain 1.18 g of the aimed product ascolorless resinous substance.

Melting point 144.0 to 147.0° C.

¹H NMR (CDCl₃, Me₄Si, 300 MHz) δ 7.3-7.55 (m, 6H), 6.49 (d, J=8.1 Hz,1H), 5.8-5.9 (m, 1H), 4.09 (d, J=17.1 Hz, 1H), 3.8-4.0 (m, 2H), 3.72 (d,J=17.1 Hz, 1H), 2.42 (s, 3H), 2.2-2.4 (m, 1H), 1.8-2.1 (m, 3H).

Synthetic Example 354-[5-(3,5-Dichlorophenyl)-5-trifluoromethyl-4,5-dihydroisoxazol-3-yl]-2-methyl-N-methyl-N-(2-tetrahydrothienyl)benzoicacid amide (Compound of the Present Invention No. 6-133)

In a solution of 0.43 g of4-[5-(3,5-dichlorophenyl)-5-trifluoromethyl-4,5-dihydroisoxazol-3-yl]-2-methyl-N-methylbenzoic acid amide synthesized similarly to Synthetic Example 29 and0.20 g of triethylamine in 5 ml of toluene, 0.45 g of trimethyl silyltrifurate was added and stirred vigorously. 10 minutes after thestirring, the reaction mixture was cooled to 0° C., 0.10 g oftetrahydrothiophen-1-oxide and 0.06 g of zinc iodide were added withstirring, and continued to stir at room temperature further for 4 days.After the completion of the reaction, 10 ml of ice water was added inthe reaction mixture, and extracted with ethyl acetate (20 ml×2), theorganic phase was dehydrated and dried with saturated sodium chlorideaqueous solution and anhydrous sodium sulfate in that order, and thesolvent was distilled under reduced pressure. The residue was purifiedwith silica gel column chromatography that was eluated with ethylacetate-hexane (1:2) to obtain 0.09 g of the aimed product as whitecrystal.

Melting point 146.0 to 151.0° C.

¹H NMR (CDCl₃, Me₄Si, 300 MHz) δ 7.4-7.7 (m, 5H), 7.15-7.25 (m, 1H),6.65-6.75 and 5.3-5.4 (m, 1H), 4.09 (d, J=17.1 Hz, 1H), 3.71 (d, J=17.1Hz, 1H), 3.12 and 2.77 (s, 3H), 2.85-3.15 (m, 2H), 2.33 and 2.30 (s,3H), 1.7-2.3 (m, 4H).

Synthetic Example 364-[5-(3,5-Dichlorophenyl)-5-trifluoromethyl-4,5-dihydroisoxazol-3-yl]-N-ethenyl-2-methylbenzoicacid amide (Compound of the Present Invention No. 5-660)

In a solution of 0.50 g of4-[5-(3,5-dichlorophenyl)-5-trifluoromethyl-4,5-dihydroisoxazol-3-yl]-2-methyl-2-methyl benzoic acid amide synthesized in Synthetic Example 29, 0.865 g ofethyl vinyl ether and 0.022 g of 1,10-phenanthroline in 10 ml of1,2-dimethoxyethane, 0.04 g of bis(trifluoroacetoxy)palladium (II) wasadded and stirred at room temperature for 19 hours. After the completionof the reaction, 30 ml of water was added in the reaction mixture, andextracted with ethyl acetate (40 ml×1), the organic phase was dehydratedand dried with saturated sodium chloride aqueous solution and anhydroussodium sulfate in that order, then filtered through silica gel, and thesolvent was distilled under reduced pressure to obtain 0.45 g of theaimed product as pale yellow resinous substance.

¹H NMR (CDCl₃, Me₄Si, 300 MHz) δ 7.3-7.6 (m, 7H), 7.05-7.25 (m, 1H),4.75 (d, J=15.6 Hz, 1H), 4.57 (d, J=8.8 Hz, 1H), 4.09 (d, J=17.4 Hz,1H), 3.70 (d, J=17.1 Hz, 1H), 2.50 (s, 3H).

Synthetic Example 374-[5-(3,5-Dichlorophenyl)-5-trifluoromethyl-4,5-dihydroisoxazol-3-yl]-2-methylbenzohydroxamicacid N-(2,2,2-trifluoroethyl)carbamic acid anhydride (Compound of thePresent Invention No. 5-663)

In a solution of 0.30 g of hydroxylamine hydrochloride in 10 ml ofmethanol, a solution of 0.65 g of potassium hydroxide in 5 ml ofmethanol was added, then a solution of 1.00 g of4-[5-(3,5-dichlorophenyl)-5-trifluoromethyl-4,5-dihydroisoxazol-3-yl]-2-methylbenzoicacid methyl ester synthesized similarly to Steps 1 to 4 of SyntheticExample 28 in 10 ml of methanol was added, and stirred at 40° C. for 1hour. After the completion of the reaction, the solvent was distilledoff under reduced pressure, 10 ml of acetic acid aqueous solution (1:1)was added in the residue, and extracted with ethyl acetate (20 ml×2),the organic phase was dehydrated and dried with saturated sodiumchloride aqueous solution and anhydrous sodium sulfate in that order,and the solvent was distilled under reduced pressure. Toluene was addedin the residue and the remaining acetic acid was distilled offazeotropically to obtain 1.01 g of crude

4-[5-(3,5-dichlorophenyl)-5-trifluoromethyl-4,5-dihydroisoxazol-3-yl]-2-methylbenzohydroxamicacid as White Crystal

In a solution of 0.16 g of carbonyl diimidazole in 2 ml oftetrahydrofuran, 0.10 g of 2,2,2-trifluoroethylamine was added, andstirred at room temperature for 1 hour. Then, a solution of 0.10 g of4-[5-(3,5-dichlorophenyl)-5-trifluoromethyl-4,5-dihydroisoxazol-3-yl]-2-methylbenzohydroxamicacid in 2 ml of tetrahydrofuran was added in the reaction mixture, andcontinued to stir at room temperature further for 1 hour. After thecompletion of the reaction, the solvent was distilled off under reducedpressure, 10 ml of water was added in the residue, and extracted withethyl acetate (10 ml×1). The organic phase was washed with 5 ml of 2Nhydrochloric acid aqueous solution, dehydrated and dried with saturatedsodium chloride aqueous solution and anhydrous sodium sulfate in thatorder, and the solvent was distilled under reduced pressure. The residuewas purified with silica gel thin-layer chromatography (Kanto ChemicalCo., Ltd.: PLC plates silica gel 60 F254 20×20 cm layer thickness 2 mm)that was developed with ethyl acetate-hexane (1:1) to obtain 0.12 g ofthe aimed product as white crystal.

Melting point 111.0 to 114.0° C.

¹H NMR (CDCl₃, Me₄Si, 300 MHz) δ 9.08 (bs, 1H), 7.4-7.6 (m, 6H), 6.07(bs, 1H), 4.08 (d, J=17.4 Hz, 1H), 3.8-3.95 (m, 2H), 3.70 (d, J=17.4 Hz,1H), 2.56 (s, 3H).

The compounds of the present invention can be produced according to theabove-mentioned production methods and working examples. The examples ofthe compounds produced similarly to Synthetic Examples 1 to 37 are shownin Tables 7 to 20 to which the present invention is not limited. In themeantime, in Tables, the indication “Et” means ethyl, hereinaftersimilarly thereto, “n-Pr” and “Pr-n” mean normal propyl, “i-Pr” and“Pr-i” mean isopropyl, “c-Pr” and “Pr-c” mean cyclopropyl, “n-Bu” and“Bu-n” mean normal butyl, “s-Bu” and “Bu-s” mean secondary butyl, “i-Bu”and “Bu-i” mean isobutyl, “t-Bu” and “Bu-t” mean tertiary butyl, “c-Bu”and “Bu-c” mean cyclobutyl, “n-Pen” and “Pen-n” means normal pentyl,c-Pen” and “Pen-c” mean cyclopentyl, “n-Hex” and “Hex-n” mean normalhexyl, “c-Hex” and “Hex-c” mean cyclohexyl, “Ph” means phenyl, “TMS”means trimethylsilyl, “•Q1” means hydrochloride, “•Q2” meansp-toluenesulfonate, “•Q3” means fumarate, “•Q4” means maleate, “•Q5”means triethylamine salt, and in Tables, aromatic heterocyclic rings ofD-1a to D-54b are the following structures, respectively.

in Tables, saturated heterocyclic rings of E-4a to E-43a are thefollowing structures, respectively,

In Tables, partially saturated heterocyclic ring of M-5a is thefollowing structure

In Tables, T-4 to T-51 are the following structures, respectively

In addition, in Tables, the number showing the substitution position ofsubstituents (X)_(m) and (Y)_(n) correspond to he position numberindicated in the following structural formulae. The indication “−” meansno-substitution.Further, in Tables, the indication of “Mw” shows the calculated value ofmolecular weight, the indication of “M⁺+H” shows the measured value ofmolecular ion peak, and “*1”, “*2” or “*3” means “resinous”, “oily” or“decomposition”, respectively.

TABLE 7

No. (X)_(m) R³ R¹ Mw M⁺ + H 1-001 — C(O)OCH₃ CH₂CF₃ 406.36 407.00 1-002— C(O)OCH₃ CH₂Ph 414.46 415.07 1-003 2-F C(O)OCH₃ CH₂CF₃ 424.35 424.991-004 2-Cl C(O)OCH₃ CH₂CF₃ 440.81 440.94 1-005 3-Br CF₃ CH₂Ph 503.31502.75 1-006 4-Br CF₃ CH₂CF₃ 495.21 494.68 1-007 4-Br CF₃ CH₂Ph 503.31502.74 1-008 3-CH₃ CF₃ CH₂CF₃ 430.34 430.91 1-009 3-CH₃ CF₃ CH₂Ph 438.44438.95 1-010 4-CH₃ CF₃ CH₂CF₃ 430.34 430.92 1-011 4-CH₃ CF₃ CH₂Ph 438.44438.91 1-012 4-Bu-t CF₃ CH₂CF₃ 472.42 472.94 1-013 4-Bu-t CF₃ CH₂Ph480.52 480.99 1-014 2-CF₃ C(O)OCH₃ CH₂CF₃ 474.36 474.87 1-015 3-CF₃ CF₃CH₂CF₃ 484.32 484.78 1-016 3-CF₃ CF₃ CH₂Ph 492.41 492.82 1-017 4-CF₃ CF₃CH₂CF₃ 484.32 484.80 1-018 4-CF₃ CF₃ CH₂Ph 492.41 492.85 1-019 2-OCH₃C(O)OCH₃ CH₂CF₃ 436.39 436.99 1-020 3-OCH₃ CF₃ CH₂CF₃ 446.34 446.891-021 3-OCH₃ CF₃ CH₂Ph 454.44 454.94 1-022 4-OCH₃ CF₃ CH₂CF₃ 446.34446.89 1-023 4-OCH₃ CF₃ CH₂Ph 454.44 454.91 1-024 4-OCH₃ C(O)OCH₃ CH₂CF₃436.39 437.00 1-025 3-OCF₃ CF₃ CH₂CF₃ 500.31 500.76 1-026 3-OCF₃ CF₃CH₂Ph 508.41 508.80 1-027 4-OCF₃ CF₃ CH₂CF₃ 500.31 500.76 1-028 4-OCF₃CF₃ CH₂Ph 508.41 508.82 1-029 4-OPh CF₃ CH₂CF₃ 508.41 508.85 1-030 4-OPhCF₃ CH₂Ph 516.51 516.88 1-031 4-SCH₃ CF₃ CH₂CF₃ 462.41 462.84 1-0324-SCH₃ CF₃ CH₂Ph 470.51 470.88 1-033 4-SO₂CH₃ CF₃ CH₂CF₃ 494.41 494.861-034 3-NHC(O)CH₃ CF₃ CH₂CF₃ 473.37 473.90 1-035 3-NHC(O)CH₃ CF₃ CH₂Ph481.47 481.93 1-036 4-NHC(O)CH₃ CF₃ CH₂CF₃ 473.37 473.81 1-0374-NHC(O)CH₃ CF₃ CH₂Ph 481.47 481.94 1-038 4-N(CH₃)₂ CF₃ CH₂CF₃ 459.38459.90 1-039 4-N(CH₃)₂ CF₃ CH₂Ph 467.48 467.94 1-040 3-NO₂ CF₃ CH₂CF₃461.31 461.82 1-041 3-NO₂ CF₃ CH₂Ph 469.41 469.86 1-042 3-TMS CF₃ CH₂CF₃488.50 488.87 1-043 3-CN CF₃ CH₂Ph 449.42 449.89 1-044 4-CN CF₃ CH₂Ph449.42 449.89 1-045 3-CHO CF₃ CH₂CF₃ 444.33 444.89 1-046 3-C(O)CH₃ CF₃CH₂CF₃ 458.35 458.82 1-047 3-C(O)CH₃ CF₃ CH₂Ph 466.45 466.81 1-0484-C(O)CH₃ CF₃ CH₂CF₃ 458.35 458.80 1-049 4-C(O)CH₃ CF₃ CH₂Ph 466.45466.86 1-050 3-C(O)OEt CF₃ CH₂CF₃ 488.38 488.89 1-051 3-C(O)OEt CF₃CH₂Ph 496.48 496.92 1-052 4-Ph CF₃ CH₂CF₃ 492.41 492.81 1-053 3,4-F₂ CF₃CH₂Pr-c 424.36 424.91 1-054 3,4-F₂ CF₃ CH₂Ph 460.40 460.87 1-055 3,5-F₂CF₃ CH₂CF₃ 452.30 452.84 1-056 3,5-F₂ CF₃ CH₂Ph 460.40 460.89 1-0573-Cl-4-F CF₃ CH₂CF₃ 468.75 468.76 1-058 3-Cl-4-F CF₃ CH₂Ph 476.85 476.801-059 2,5-Cl₂ CF₃ CH₂CF₃ 485.21 484.79 1-060 2,5-Cl₂ CF₃ CH₂Ph 493.30492.82 1-061 2,5-Cl₂ CF₃ CH₂(D-47a) 494.29 493.84 1-062 3,4-Cl₂ CF₃ Et431.24 430.93 1-063 3,4-Cl₂ CF₃ n-Pr 445.27 444.94 1-064 3,4-Cl₂ CF₃i-Pr 445.27 444.94 1-065 3,4-Cl₂ CF₃ n-Bu 459.29 458.97 1-066 3,4-Cl₂CF₃ CH₂Pr-c 457.28 456.94 1-067 3,4-Cl₂ CF₃ s-Bu 459.29 458.93 1-0683,4-Cl₂ CF₃ t-Bu 459.29 458.92 1-069 3,4-Cl₂ CF₃ c-Bu 457.27 456.791-070 3,4-Cl₂ CF₃ n-Pen 473.32 473.02 1-071 3,4-Cl₂ CF₃ CH₂Bu-s 473.32472.82 1-072 3,4-Cl₂ CF₃ CH₂Bu-t 473.32 472.94 1-073 3,4-Cl₂ CF₃CH(CH₃)Pr-n 473.32 472.94 1-074 3,4-Cl₂ CF₃ c-Pen 471.31 470.99 1-0753,4-Cl₂ CF₃ n-Hex 487.35 486.96 1-076 3,4-Cl₂ CF₃ c-Hex 485.33 484.931-077 3,4-Cl₂ CF₃ CH₂Hex-c 499.35 498.88 1-078 3,4-Cl₂ CF₃ CH₂(T-39)539.42 538.88 1-079 3,4-Cl₂ CF₃ CH₂CH₂Cl 465.69 464.73 1-080 3,4-Cl₂ CF₃CH₂CF₃ 485.21 484.85 1-081 3,4-Cl₂ CF₃ CH₂CF₂CF₂CF₃ 585.23 584.65 1-0823,4-Cl₂ CF₃ CH₂CH(CH₃)OH(R) 461.26 460.78 1-083 3,4-Cl₂ CF₃CH₂CH(CH₃)OH(S) 461.26 460.82 1-084 3,4-Cl₂ CF₃ CH₂CH(CH₃)OC(O)NHEt(S)532.34 531.78 1-085 3,4-Cl₂ CF₃ CH(CH₃)CH₂OCH₃ 475.29 474.94 1-0863,4-Cl₂ CF₃ CH₂CH(Et)OH 475.29 474.82 1-087 3,4-Cl₂ CF₃ CH(Et)CH₂OCH₃489.32 488.95 1-088 3,4-Cl₂ CF₃ CH₂CH(OCH₃)₂ 491.29 490.80 1-089 3,4-Cl₂CF₃ CH₂CH₂CH₂OH 461.27 460.97 1-090 3,4-Cl₂ CF₃ CH₂CH₂CH₂OCH₃ 475.29474.98 1-091 3,4-Cl₂ CF₃ CH₂(T-13) 515.35 514.80 1-092 3,4-Cl₂ CF₃CH₂(E-11c) 517.33 516.79 1-093 3,4-Cl₂ CF₃ CH₂CH₂SCH₃ 477.33 476.751-094 3,4-Cl₂ CF₃ CH₂CH₂SBu-t 519.41 518.96 1-095 3,4-Cl₂ CF₃CH₂CH₂CH₂SCH₃ 491.35 490.92 1-096 3,4-Cl₂ CF₃ CH₂CH₂NHC(O)OBu-t 546.37545.75 1-097 3,4-Cl₂ CF₃ CH₂CH₂CH₂Si(OCH₃)₃ 565.44 564.77 1-098 3,4-Cl₂CF₃ CH₂CH₂CH₂Si(CH₃)(OEt)₂ 577.49 576.79 1-099 3,4-Cl₂ CF₃ CH₂C(O)OCH₃475.25 474.89 1-100 3,4-Cl₂ CF₃ CH₂CH₂C(O)OCH₃ 489.28 488.80 1-1013,4-Cl₂ CF₃ CH₂C(O)NH₂ 460.24 459.74 1-102 3,4-Cl₂ CF₃ CH₂CH═CH₂ 443.25442.81 1-103 3,4-Cl₂ CF₃ CH₂CH₂(T-17) 511.36 510.76 1-104 3,4-Cl₂ CF₃CH₂C≡CH 441.24 440.91 1-105 3,4-Cl₂ CF₃ CH₂Ph 493.31 492.86 1-1063,4-Cl₂ CF₃ CH₂(Ph-2-F) 511.30 510.80 1-107 3,4-Cl₂ CF₃ CH₂(Ph-3-F)511.30 510.81 1-108 3,4-Cl₂ CF₃ CH₂(Ph-2-Cl) 527.75 526.74 1-109 3,4-Cl₂CF₃ CH₂(Ph-3-Cl) 527.75 526.75 1-110 3,4-Cl₂ CF₃ CH₂(Ph-2-CH₃) 507.33506.78 1-111 3,4-Cl₂ CF₃ CH₂(Ph-4-CH₃) 507.33 506.73 1-112 3,4-Cl₂ CF₃CH₂(Ph-4-Bu-t) 549.41 548.77 1-113 3,4-Cl₂ CF₃ CH₂(Ph-2-CF₃) 561.30560.72 1-114 3,4-Cl₂ CF₃ CH₂(Ph-3-CF₃) 561.30 560.69 1-115 3,4-Cl₂ CF₃CH₂(Ph-4-CF₃) 561.30 560.97 1-116 3,4-Cl₂ CF₃ CH₂(Ph-2-OCH₃) 523.33522.77 1-117 3,4-Cl₂ CF₃ CH₂(Ph-3-OCH₃) 523.33 522.74 1-118 3,4-Cl₂ CF₃CH₂(Ph-4-OCH₃) 523.33 522.68 1-119 3,4-Cl₂ CF₃ CH₂(Ph-3-OCF₃) 577.30576.69 1-120 3,4-Cl₂ CF₃ CH₂(Ph-4-SO₂CH₃) 571.40 570.71 1-121 3,4-Cl₂CF₃ CH₂[Ph-4-N(CH₃)₂] 536.37 535.81 1-122 3,4-Cl₂ CF₃ CH₂(Ph-3-NO₂)538.30 537.64 1-123 3,4-Cl₂ CF₃ CH₂(Ph-4-NO₂) 538.30 537.66 1-1243,4-Cl₂ CF₃ CH₂[Ph-4-C(O)OCH₃] 551.34 550.74 1-125 3,4-Cl₂ CF₃CH₂(Ph-2,5-F₂) 529.29 528.72 1-126 3,4-Cl₂ CF₃ CH₂(Ph-2,6-F₂) 529.29528.81 1-127 3,4-Cl₂ CF₃ CH₂(Ph-3,5-F₂) 529.29 528.73 1-128 3,4-Cl₂ CF₃CH₂(Ph-3-Cl-4-F) 545.74 544.67 1-129 3,4-Cl₂ CF₃ CH₂(Ph-2,3-Cl₂) 562.20560.72 1-130 3,4-Cl₂ CF₃ CH₂(Ph-2,4-Cl₂) 562.20 560.72 1-131 3,4-Cl₂ CF₃CH₂(Ph-2,5-Cl₂) 562.20 560.72 1-132 3,4-Cl₂ CF₃ CH₂(Ph-2,6-Cl₂) 562.20560.73 1-133 3,4-Cl₂ CF₃ CH₂(Ph-3,5-Cl₂) 562.20 560.64 1-134 3,4-Cl₂ CF₃CH₂(Ph-3-CF₃-4-F) 579.29 578.70 1-135 3,4-Cl₂ CF₃ CH₂[Ph-3,4-(OCH₃)₂]553.36 552.76 1-136 3,4-Cl₂ CF₃ CH₂(Ph-3-OCH₂O-4) 537.31 536.73 1-1373,4-Cl₂ CF₃ CH₂(1-Naph) 543.36 542.80 1-138 3,4-Cl₂ CF₃ CH(CH₃)Ph 507.34506.88 1-139 3,4-Cl₂ CF₃ CH(CH₃)(Ph-3-Cl) 541.78 540.70 1-140 3,4-Cl₂CF₃ C(CH₃)₂Ph 521.37 520.99 1-141 3,4-Cl₂ CF₃ CH₂CH₂Ph 507.34 507.011-142 3,4-Cl₂ CF₃ CH₂CH₂(Ph-4-OPh) 599.44 598.95 1-143 3,4-Cl₂ CF₃CH₂CH(CH₃)Ph 521.37 520.93 1-144 3,4-Cl₂ CF₃ CH₂CHPh 583.43 582.79 1-1453,4-Cl₂ CF₃ CH(CH₃)CH₂(Ph-4-Cl) 555.81 554.78 1-146 3,4-Cl₂ CF₃ T-9519.35 518.88 1-147 3,4-Cl₂ CF₃ CH₂CH₂CH₂Ph 521.37 520.97 1-148 3,4-Cl₂CF₃ CH₂CH₂SCH₂Ph 553.43 552.75 1-149 3,4-Cl₂ CF₃ CH₂C(O)(Ph-4-OCH₃)551.34 550.66 1-150 3,4-Cl₂ CF₃ CH₂(D-1c)CH₃ 497.29 496.80 1-151 3,4-Cl₂CF₃ CH₂(D-3a) 499.33 498.70 1-152 3,4-Cl₂ CF₃ CH₂(D-3b)CH₃ 513.36 512.741-153 3,4-Cl₂ CF₃ CH₂(D-47a) 494.29 493.84 1-154 3,4-Cl₂ CF₃ CH₂(D-47f)596.74 595.79 1-155 3,4-Cl₂ CF₃ CH₂(D-48a) 494.29 493.84 1-156 3,4-Cl₂CF₃ CH₂(D-49a) 494.29 493.86 1-157 3,4-Cl₂ CF₃ CH₂(D-53b)CH₃ 509.31508.78 1-158 3,4-Cl₂ CF₃ CH₂CH₂(D-3a) 513.36 512.71 1-159 3,4-Cl₂ CF₃CH₂CH₂(D-47a) 508.32 507.76 1-160 3,4-Cl₂ CF₃ CH₂CH₂(D-48a) 508.32507.77 1-161 3,4-Cl₂ CF₃ CH₂CH₂CH₂(D-24a) 511.32 510.84 1-162 3,4-Cl₂CF₃ T-21 472.24 471.77 1-163 3,4-Cl₂ CF₃ T-22 488.31 487.72 1-1643,4-Cl₂ CF₃ (D-8b)CH₃ 484.25 483.75 1-165 3,4-Cl₂ CF₃ D-11c 581.35580.66 1-166 3,4-Cl₂ CF₃ D-21a 486.29 485.70 1-167 3,4-Cl₂ CF₃(D-21b)CH₃ 500.32 499.70 1-168 3,4-Cl₂ CF₃ (D-21c)CH₃ 500.32 499.701-169 3,4-Cl₂ CF₃ (D-21c)NO₂ 531.29 530.60 1-170 3,4-Cl₂ CF₃ D-25d533.33 532.73 1-171 3,4-Cl₂ CF₃ D-48a 480.27 479.76 1-172 3,4-Cl₂ CF₃D-49a 480.27 479.76 1-173 3,4-Cl₂ CF₃ OPr-n 461.27 460.94 1-174 3,4-Cl₂CF₃ N(CH₃)₂ 446.26 445.92 1-175 3,5-Cl₂ CF₃ CH₂Pr-c 457.27 456.83 1-1763,5-Cl₂ CF₃ CH₂CH₂CF₃ 499.23 498.79 1-177 3,5-Cl₂ CF₃ CH₂CH₂OEt 475.29474.86 1-178 3,5-Cl₂ CF₃ CH₂CH₂OCH₂CH₂OH 491.29 490.78 1-179 3,5-Cl₂ CF₃CH₂CH(CH₃)OH 461.27 460.88 1-180 3,5-Cl₂ CF₃ CH₂CH₂CH₂OEt 489.31 488.901-181 3,5-Cl₂ CF₃ CH₂CH₂CH₂O-Pr-i 503.34 502.86 1-182 3,5-Cl₂ CF₃CH₂CH₂SEt 491.35 490.99 1-183 3,5-Cl₂ CF₃ CH₂(Ph-3-Br) 572.20 570.681-184 3,5-Cl₂ CF₃ CH₂(Ph-3-OCH₃) 523.33 522.80 1-185 3,5-Cl₂ CF₃CH₂(Ph-4-OCH₃) 523.33 522.74 1-186 3,5-Cl₂ CF₃ CH₂(Ph-4-OCF₃) 577.30576.75 1-187 3,5-Cl₂ CF₃ CH₂(Ph-4-SO₂NH₂) 572.38 571.78 1-188 3,5-Cl₂CF₃ CH₂(Ph-3-NO₂) 538.30 537.76 1-189 3,5-Cl₂ CF₃ CH₂(Ph-4-NO₂) 538.30537.76 1-190 3,5-Cl₂ CF₃ CH₂CH₂(Ph-3-Cl) 541.78 540.71 1-191 3,5-Cl₂ CF₃CH₂CH₂(Ph-4-OCH₃) 537.36 536.79 1-192 3,5-Cl₂ CF₃ CH₂CH₂(Ph-3,4-Cl₂)576.22 574.60 1-193 3,5-Cl₂ CF₃ CH₂CH₂[Ph-3,4-(OCH₃)₂] 567.38 566.771-194 3,5-Cl₂ CF₃ CH₂CH₂OPh 523.33 522.85 1-195 3,5-Cl₂ CF₃ Ph-4-OCH₃509.30 508.75 1-196 3,5-Cl₂ CF₃ (D-21b)CH₂C(O)OEt 572.38 571.70 1-1973,5-Cl₂ CF₃ (D-21c)Br 565.19 563.59 1-198 3,5-Cl₂ CF₃(D-21c)SO₂(Ph-4-NO₂) 671.45 670.55 1-199 3,5-Cl₂ CF₃ D-21d 514.35 513.721-200 3,5-Cl₂ CF₃ D-21e 536.35 535.70 1-201 3,5-Cl₂ CF₃ D-21f 570.80569.68 1-202 3,5-Cl₂ CF₃ D-21g 570.80 569.68 1-203 3,5-Cl₂ CF₃ D-21h566.38 565.71 1-204 3,5-Cl₂ CF₃ D-21i 566.38 565.76 1-205 3,5-Cl₂ CF₃D-21j 581.35 580.69 1-206 3,5-Cl₂ CF₃ NHPh 494.29 493.81 1-207 3,5-Br₂CF₃ CH₂CF₃ 574.11 572.49 1-208 3,5-Br₂ CF₃ CH₂Ph 582.21 580.61 1-2093-CH₃-4-F CF₃ CH₂Ph 456.43 456.87 1-210 3,4-(CH₃)₂ CF₃ CH₂CF₃ 444.37444.89 1-211 3,4-(CH₃)₂ CF₃ CH₂Ph 452.47 452.94 1-212 3,5-(CH₃)₂ CF₃CH₂CF₃ 444.37 444.86 1-213 3,5-(CH₃)₂ CF₃ CH₂Ph 452.47 452.95 1-2143,5-(CF₃)₂ CF₃ CH₂CF₃ 552.31 552.72 1-215 3,5-(CF₃)₂ CF₃ CH₂Ph 560.41560.76 1-216 3-OEt-4-Cl CF₃ CH₂CF₃ 494.81 494.76 1-217 3-OEt-4-Cl CF₃CH₂Ph 502.91 502.81 1-218 3,4-(OCH₃)₂ CF₃ CH₂CF₃ 476.37 476.83 1-2193,4-(OCH₃)₂ CF₃ CH₂Ph 484.47 484.90 1-220 3-OCH₂O-4 CF₃ CH₂Pr-c 432.39432.89 1-221 3-OCH₂O-4 CF₃ CH₂Ph 468.42 468.86 1-222 3,5-(CHO)₂ CF₃CH₂CF₃ 472.34 472.92 1-223 3-CH═CHCH═CH-4 CF₃ CH₂CF₃ 466.38 466.83 1-2243-CH═CHCH═CH-4 CF₃ CH₂Ph 474.47 474.86 1-225 3,4,5-F₃ CF₃ CH₂CF₃ 470.29470.77 1-226 3,4,5-F₃ CF₃ CH₂Ph 478.39 478.82

TABLE 8

No. (X)_(m) (Y)_(n) R² R¹ Mw M⁺ + H 2-001 3,4-F₂ — CH₃ CH₂Ph 474.42474.88 2-002 3,4-Cl₂ — CH₃ CH₃ 431.24 430.91 2-003 3,4-Cl₂ — Et Et459.29 458.94 2-004 3,4-Cl₂ — CH₃ n-Bu 473.32 472.97 2-005 3,4-Cl₂ — CH₃i-Bu 473.32 472.89 2-006 3,4-Cl₂ — —CH₂CH₂CH₂CH₂— 457.28 456.85 2-0073,4-Cl₂ — —CH₂CH₂CH₂CH₂CH₂— 471.31 470.84 2-008 3,4-Cl₂ ——CH₂CH₂CH₂CH₂CH(CH₃)— 485.33 484.83 2-009 3,4-Cl₂ ——CH₂CH₂CH₂CH(CH₃)CH₂— 485.33 484.82 2-010 3,4-Cl₂ ——CH₂CH(CH₃)CH₂CH(CH₃)CH₂— 499.35 498.82 2-011 3,4-Cl₂ — —CH₂CH₂OCH₂CH₂—473.28 472.75 2-012 3,4-Cl₂ — —CH₂CH(CH₃)OCH(CH₃)CH₂— 501.33 500.772-013 3,4-Cl₂ — —CH₂CH₂SCH₂CH₂— 489.34 488.74 2-014 3,4-Cl₂ ——CH₂CH₂N(CHO)CH₂CH₂— 500.30 499.76 2-015 3,4-Cl₂ — CH₃ CH₂CH═CH₂ 457.27456.87 2-016 3,4-Cl₂ — CH₂CH═CH₂ CH₂CH═CH₂ 483.31 482.85 2-017 3,4-Cl₂ —CH₃ CH₂C≡CH 455.26 454.86 2-018 3,4-Cl₂ — CH₃ CH₂Ph 507.34 506.93 2-0193,4-Cl₂ — Et CH₂(D-48e)Cl 556.79 555.73 2-020 3,5-Cl₂ — Et Et 459.29458.85 2-021 3,5-Cl₂ — CH₃ CH₂Ph 507.33 506.79 2-022 3,5-Cl₂ — Et CH₂Ph521.36 520.79 2-023 3,5-Cl₂ — CH₂Ph CH₂Ph 583.43 582.79 2-024 3,5-Cl₂2-CH₃ H CH₂CH₂OH 461.26 460.99 2-025 3,5-Cl₂ 2-CH₃ H CH₂CH₂OPr-n 503.34502.99 2-026 3,5-Cl₂ 2-CH₃ H CH₂CH₂OPr-i 503.34 502.98 2-027 3,5-Cl₂2-CH₃ H CH₂CH₂OCH₂CH₂OH 505.31 504.95 2-028 3,5-Cl₂ 2-CH₃ H CH₂CH₂OPh537.36 536.94 2-029 3,5-Cl₂ 2-CH₃ H CH(CH₃)CH₂OCH₃ 489.31 488.98 2-0303,5-Cl₂ 2-CH₃ H CH₂CH₂N(CH₃)₂ 488.33 487.98 2-031 3,5-Cl₂ 2-CH₃ HCH(Ph)C(O)OCH₃(R) 565.37 564.84 2-032 3,5-Cl₂ 2-CH₃ H CH(Ph)C(O)OCH₃(S)565.37 564.92 2-033 3,5-Cl₂ 2-CH₃ H CH₂CH₂C(O)OCH₃ 503.30 502.91 2-0343,5-Cl₂ 2-CH₃ H CH₂(Ph-4-OCH₃) 537.36 536.98 2-035 3,5-Cl₂ 2-CH₃ HCH₂(Ph-4-CN) 532.34 531.94 2-036 3,5-Cl₂ 2-CH₃ H CH₂CH₂(D-47a) 522.35521.94 2-037 3,5-Cl₂ 2-CH₃ H T-29b 562.32 559.80* 2-038 3,5-Cl₂ 2-CH₃ HNHCH₂C(O)OEt 518.31 517.93 2-039 3,5-Cl₂ 2-CH₃ H NHCHO 460.23 457.86*2-040 3,5-Cl₂ 2-CH₃ H NHC(O)CH₂(D-3a) 556.38 553.71* 2-041 3,5-Cl₂ 2-CH₃H N(CH₃)C(S)NH₂ 505.34 504.82 2-042 3,5-Cl₂ 2-CH₃ H N(CH₃)C(S)NHCH₃519.37 518.88 2-043 3,5-Cl₂ 2-CH₃ H T-40 530.37 529.98 2-044 3,5-Cl₂2-CH₃ H NH(Ph-2-F) 526.31 525.92 2-045 3,5-Cl₂ 2-CH₃ H NH(Ph-3-F) 526.31525.92 2-046 3,5-Cl₂ 2-CH₃ H NH(Ph-4-F) 526.31 523.89* 2-047 3,5-Cl₂2-CH₃ H NH(Ph-4-Br) 587.22 585.91 2-048 3,5-Cl₂ 2-CH₃ H NH(Ph-4-CH₃)522.35 521.93 2-049 3,5-Cl₂ 2-CH₃ H NH(Ph-4-Pr-i) 550.40 549.94 2-0503,5-Cl₂ 2-CH₃ H NH(Ph-4-OCF₃) 592.32 591.97 2-051 3,5-Cl₂ 2-CH₃ HNH(Ph-4-CN) 533.33 533.01 2-052 3,5-Cl₂ 2-CH₃ H N(CH₃)(D-47d)CF₃ 591.33590.99 2-053 3,5-Cl₂ 2-CH₃ H N═CHC(CH₃)═CHPh 560.39 559.95 2-054 3,5-Cl₂2-CH₃ H D-47a 494.29 493.94 2-055 3,5-Cl₂ 2-CH₃ H D-49a 494.29 493.972-056 3-OCH₂O-4 — CH₃ CH₂Ph 482.45 482.86 2-057 3,5-Cl₂ 2-CH₃C(O)OCH₃CH₂CH═CH₂ 515.31 514.97 2-058 3,5-Cl₂ 2-CH₃ C(O)OPr-i CH₂CH═CH₂543.36 541.04* 2-059 3,5-Cl₂ 2-CH₃ H C(O)OCH₂CH₂Cl 523.72 522.84 2-0603,5-Cl₂ 2-CH₃ H C(O)OCH₂CHCl₂ 558.16 554.92* 2-061 3,5-Cl₂ 2-CH₃ HC(O)OCH₂CCl₃ 592.61 588.88* 2-062 3,5-Cl₂ 2-CH₃ H C(O)OCH₂CH₂CF₃ 557.27557.03 2-063 3,5-Cl₂ 2-CH₃ H C(O)OCH(CH₂Cl)₂ 572.19 570.94* 2-0643,5-Cl₂ 2-CH₃ H C(O)OCH(CF₃)₂ 611.24 608.86* 2-065 3,5-Cl₂ 2-CH₃ HC(O)OCH(CH₃)CHClCH₃ 551.77 548.95* 2-066 3,5-Cl₂ 2-CH₃ HC(O)OCH₂CH₂CH₂CH₂Cl 551.77 550.99 2-067 3,5-Cl₂ 2-CH₃ HC(O)OCH₂C(CF₃)₂CH₃ 639.29 636.95* 2-068 3,5-Cl₂ 2-CH₃ H T-25 501.33502.05 2-069 3,5-Cl₂ 2-CH₃ H (D-21c)C(O)OEt 571.38 572.04In Table above, the indication of “*” shows the measured value ofmolecular ion peak of M+H measured with negative mode.

TABLE 9

No. (X)_(m) R³ R¹ m. p. (° C.) 3-001 — CF₃ CH₂CF₃ 172.0-173.0 3-002 3-ClCF₃ CH₂CF₃ 157.0-158.0 3-003 3-Cl CF₃ CH₂Ph 168.0-169.0 3-004 4-Cl CF₃CH₂CF₃ 190.0-191.0 3-005 4-Cl CF₃ CH₂Ph 212.0-214.0 3-006 3-Br CF₃CH₂CF₃ 132.0-135.0 3-007 3-OCF₃ CF₃ CH₂(D-47a) 145.0-147.0 3-0083-OCH₂Ph CF₃ CH₂CF₃ 146.0-149.0 3-009 3-OCH₂(Ph-2-Cl) CF₃ CH₂CF₃158.0-159.0 3-010 3-OCH₂(Ph-2-Cl) CF₃ CH₂(D-47a) *1 3-011 3-SEt CF₃CH₂CF₃ 105.0-106.0 3-012 3-CN CF₃ CH₂CF₃ 93.0-96.0 3-013 4-CN CF₃ CH₂CF₃149.0-151.0 3-014 3-CH═NOH CF₃ CH₂CF₃ 168.0-169.0 3-015 3-CH═NOCH₃ CF₃CH₂CF₃ *1 3-016 4-C(CH₃)═NOCH₃(E) CF₃ CH₂CF₃ 160.0-162.0 3-0174-C(CH₃)═NOCH₃(Z) CF₃ CH₂CF₃ *1 3-018 3,4-F₂ CF₃ CH₂CF₃ 150.0-152.03-019 2,4-Cl₂ CF₃ CH₂CF₃ 149.0-151.0 3-020 3,4-Cl₂ H CH₂CF₃ 161.0-162.03-021 3,4-Cl₂ H CH₂Ph 147.0-148.0 3-022 3,4-Cl₂ CH₃ CH₂Pr-c 157.0-158.03-023 3,4-Cl₂ CH₃ CH₂CF₃ 120.0-122.0 3-024 3,4-Cl₂ CH₃ CH₂Ph 153.0-155.03-025 3,4-Cl₂ CF₃ CH₃ 139.0-140.0 3-026 3,4-Cl₂ CF₃ c-Pr 193.0-194.03-027 3,4-Cl₂ CF₃ i-Bu 158.0-159.0 3-028 3,4-Cl₂ CF₃ CH₂Bu-c 177.0-179.03-029 3,4-Cl₂ CF₃ CH₂CH(Et)Bu-n 125.0-127.0 3-030 3,4-Cl₂ CF₃ CH₂CF₂CF₃171.0-173.0 3-031 3,4-Cl₂ CF₃ CH₂(E-4a) 136.0-138.0 3-032 3,4-Cl₂ CF₃CH(CH₃)CH₂SCH₃ 145.0-147. 3-033 3,4-Cl₂ CF₃ C(CH₃)₂CH₂SCH₃ 150.0-152.03-034 3,4-Cl₂ CF₃ C(CH₃)₂CH₂S(O)CH₃ *1 3-035 3,4-Cl₂ CF₃C(CH₃)₂CH₂SO₂CH₃ 161.0-163.0 3-036 3,4-Cl₂ CF₃ CH₂CH₂CH₂C(O)OEt105.0-107.0 3-037 3,4-Cl₂ CF₃ CH₂(Ph-4-F) 155.0-156.0 3-038 3,4-Cl₂ CF₃CH₂(Ph-4-Cl) 191.0-193.0 3-039 3,4-Cl₂ CF₃ CH₂(Ph-3-CH₃) 198.0-200.03-040 3,4-Cl₂ CF₃ CH₂(Ph-3,4-Cl₂) 161.0-162.0 3-041 3,4-Cl₂ CF₃CH₂CH(Ph)OH 211.0-213.0 3-042 3,4-Cl₂ CF₃ CH₂C(O)(Ph-4-Br) 193.0-195.03-043 3,4-Cl₂ CF₃ CH₂(D-1a) 179.0-180.0 3-044 3,4-Cl₂ CF₃ CH₂(D-48e)Cl154.0-157.0 3-045 3,4-Cl₂ CF₃ CH₂(D-50d) 183.0-186.0 3-046 3,4-Cl₂ CF₃CH₂CH₂(D-49a) 113.0-116.0 3-047 3,4-Cl₂ CF₃ NHPh 160.0-162.0 3-0483,4-Cl₂ CF₃ Ph 208.0-210.0 3-049 3,4-Cl₂ CF₃ Ph-2-CH₃-4-Cl 237.0-238.03-050 3,4-Cl₂ CF₃ D-35a 238.0-241.0 3-051 3,4-Cl₂ CF₃ D-47a 167.0-169.03-052 3,4-Cl₂ CN CH₂CF₃ 162.0-164.0 3-053 3,4-Cl₂ Ph CH₂Pr-c 153.0-154.03-054 3,4-Cl₂ Ph CH₂CF₃ 157.0-158.0 3-055 3,4-Cl₂ Ph CH₂Ph 173.0-175.03-056 3,5-Cl₂ c-Pr CH₂CF₃ 144.0-145.0 3-057 3,5-Cl₂ CF₃ H 256.0-258.03-058 3,5-Cl₂ CF₃ i-Bu 167.0-170.0 3-059 3,5-Cl₂ CF₃ CH₂Cl *1 3-0603,5-Cl₂ CF₃ CH₂CF₃ 94.0-96.0 3-061 3,5-Cl₂ CF₃ CH₂(T-4) 84.0-87.0 3-0623,5-Cl₂ CF₃ CH₂OH 254.0-260.0 3-063 3,5-Cl₂ CF₃ CH₂CH(OCH₃)₂ 198.0-200.03-064 3,5-Cl₂ CF₃ CH₂CH(OEt)₂ *1 3-065 3,5-Cl₂ CF₃ CH₂CH(CH₃)OC(O)NHEt127.0-129.0 3-066 3,5-Cl₂ CF₃ CH₂CH(CH₃)OC(O)NH(Ph-4-F) 162.0-165.03-067 3,5-Cl₂ CF₃ CH₂CH(OH)CH₂OH *1 3-068 3,5-Cl₂ CF₃ CH₂(E-4a)123.5-126.0 3-069 3,5-Cl₂ CF₃ CH₂(E-5a) *1 3-070 3,5-Cl₂ CF₃ CH₂(E-10a)152.0-153.0 3-071 3,5-Cl₂ CF₃ CH₂(E-10b)CH₃ 151.0-153.0 3-072 3,5-Cl₂CF₃ CH₂(E-32a) *1 3-073 3,5-Cl₂ CF₃ C(CH₃)₂CH₂SCH₃ 91.0-92.0 3-0743,5-Cl₂ CF₃ C(CH₃)₂CH₂SO₂CH₃ *1 3-075 3,5-Cl₂ CF₃ CH₂(E-18a) 124.0-126.03-076 3,5-Cl₂ CF₃ CH₂(E-18c) 253.0-255.0 3-077 3,5-Cl₂ CF₃ CH₂CHO *13-078 3,5-Cl₂ CF₃ CH₂CH═NOH *1 3-079 3,5-Cl₂ CF₃ CH₂CH═NOCH₃ *1 3-0803,5-Cl₂ CF₃ CH₂C(CH₃)═NOCH₃ 71.0-75.0 3-081 3,5-Cl₂ CF₃ CH₂CN145.0-151.0 3-082 3,5-Cl₂ CF₃ CH₂C(O)OH *1 3-083 3,5-Cl₂ CF₃ CH₂C(O)OCH₃*1 3-084 3,5-Cl₂ CF₃ CH₂C(O)NH₂ 100.0-107.0 3-085 3,5-Cl₂ CF₃CH₂C(O)NHCH₂CH₂Cl 161.5-165.0 3-086 3,5-Cl₂ CF₃ CH₂C(O)NHCH₂CF₃108.0-114.0 3-087 3,5-Cl₂ CF₃ CH₂C(S)NH₂ *1 3-088 3,5-Cl₂ CF₃CH₂C(═NOH)NH₂•HCl 140.0-144.5 3-089 3,5-Cl₂ CF₃ CH₂CH═CH₂ *1 3-0903,5-Cl₂ CF₃ CH₂C(CH₃)═CH₂ 133.0-136.0 3-091 3,5-Cl₂ CF₃ CH₂CCl═CH₂121.0-123.0 3-092 3,5-Cl₂ CF₃ CH₂CH═CCl₂ 118.0-120.0 3-093 3,5-Cl₂ CF₃CH₂CCl═CHCl 153.0-154.0 3-094 3,5-Cl₂ CF₃ CH₂C≡CH 144.0-146.0 3-0953,5-Cl₂ CF₃ CH₂Ph 174.0-177.0 3-096 3,5-Cl₂ CF₃ CH₂(Ph-4-Br) 203.0-205.03-097 3,5-Cl₂ CF₃ CH₂(Ph-4-SCH₃) 182.0-184.0 3-098 3,5-Cl₂ CF₃CH₂[Ph-4-S(O)CH₃] 170.0-174.0 3-099 3,5-Cl₂ CF₃ CH₂(Ph-4-SO₂CH₃)214.0-216.0 3-100 3,5-Cl₂ CF₃ CH₂(Ph-2-NO₂) 165.0-167.0 3-101 3,5-Cl₂CF₃ CH₂(D-1a) 178.5-181.0 3-102 3,5-Cl₂ CF₃ CH₂(D-3a) 201.0-202.0 3-1033,5-Cl₂ CF₃ CH₂(D-3d)Cl 144.0-146.0 3-104 3,5-Cl₂ CF₃ CH₂(D-10b)Cl87.0-95.0 3-105 3,5-Cl₂ CF₃ CH₂(D-15a)CH₃ 154.0-155.0 3-106 3,5-Cl₂ CF₃CH₂(D-16b)Cl 224.0-225.0 3-107 3,5-Cl₂ CF₃ CH₂(D-16c)Cl *1 3-108 3,5-Cl₂CF₃ CH₂(D-16d) *1 3-109 3,5-Cl₂ CF₃ CH₂(D-17a)CH₃ 59.0-61.0 3-1103,5-Cl₂ CF₃ CH₂(D-17b)Cl *1 3-111 3,5-Cl₂ CF₃ CH₂(D-21a) 178.0-179.03-112 3,5-Cl₂ CF₃ CH₂(D-22a) 156.0-158.0 3-113 3,5-Cl₂ CF₃ CH₂(D-22b)Cl94.0-96.0 3-114 3,5-Cl₂ CF₃ CH₂(D-22b)CH₃ *1 3-115 3,5-Cl₂ CF₃CH₂(D-23a) 191.0-193.0 3-116 3,5-Cl₂ CF₃ CH₂(D-23b)Cl 165.0-167.0 3-1173,5-Cl₂ CF₃ CH₂(D-24b) 218.0-220.0 3-118 3,5-Cl₂ CF₃ CH₂(D-24c) *1 3-1193,5-Cl₂ CF₃ CH₂(D-25a)CH₃ *1 3-120 3,5-Cl₂ CF₃ CH₂(D-27a)CH₃ *1 3-1213,5-Cl₂ CF₃ CH₂(D-29b)CH₃ *1 3-122 3,5-Cl₂ CF₃ CH₂(D-34a) *1 3-1233,5-Cl₂ CF₃ CH₂(D-35a) 157.5-161.0 3-124 3,5-Cl₂ CF₃ CH₂(D-38a)224.5-226.0 3-125 3,5-Cl₂ CF₃ CH₂(D-47a) 150.0-151.0 3-126 3,5-Cl₂ CF₃CH₂(D-47c)Cl 124.0-126.0 3-127 3,5-Cl₂ CF₃ CH₂(D-47e)CH₃ *2 3-1283,5-Cl₂ CF₃ CH₂(D-47i) 121.0-124.0 3-129 3,5-Cl₂ CF₃ CH₂(D-48e)Cl159.5-163.0 3-130 3,5-Cl₂ CF₃ CH₂(D-50d) 250.0-255.0 3-131 3,5-Cl₂ CF₃CH₂(D-53b)CH₃ *1 3-132 3,5-Cl₂ CF₃ CH(CH₃)Ph 137.5-141.0 3-133 3,5-Cl₂CF₃ C(O)(D-47a) *1 3-134 3,5-Cl₂ CF₃ OCH₃ *1 3-135 3,5-Cl₂ CF₃ NH(D-47a)*1 3-136 3,5-Cl₂ CF₃ NH(D-50a) 202.0-204.0 3-137 3,5-Cl₂ CF₃NH(D-50b)CF₃ 146.0-149.0 3-138 3,5-Cl₂ CF₃ NH(D-54b)Cl 124.0-130.0 3-1393,5-Cl₂ CF₃ N(CH₃)Ph 174.0-178.0 3-140 3,5-Cl₂ CF₃ D-21a 268.0-273.03-141 3-CH₃-4-F CF₃ CH₂CF₃ 151.0-152.0 3-142 3-Cl-5-CH₃ CF₃ CH₂CF₃74.0-76.0 3-143 3-Cl-5-CH₃ CF₃ CH₂(D-47a) *1 3-144 3-Cl-4-OCH₃ CF₃CH₂CF₃ 135.0-138.0 3-145 3-CF₃-5-OCH₃ CF₃ CH₂CF₃ 161.0-162.0 3-1463-OCH₂O-4 CF₃ CH₂CF₃ 149.0-151.0 3-147 2-F-3-CH₃-5-Cl CF₃ CH₂CF₃ *13-148 3,5-Cl₂ CF₃ CH₂(D-34b)CH₃ 143.0-144.5 3-149 3,5-Cl₂ CF₃ NH₂170.0-172.0 3-150 3,5-Cl₂ CF₃ Ph-4-F 166.0-168.0 3-151 3,5-Cl₂ CF₃ E-4a210.0-213.0

TABLE 10

m. p. No. (X)_(m) R³ R² R¹ (° C.) 4-001 3,4-Cl₂ CF₃—CH₂CH₂CH(CH₃)CH₂CH₂— 132.0- 134.0 4-002 3,4-Cl₂ CF₃—CH₂CH₂CH₂CH₂CH₂CH₂— 160.0- 163.0 4-003 3,5-Cl₂ CF₃ CH₂OCH₃ CH₂ *1(D-47a) 4-004 3,5-Cl₂ CF₃ CH₂OEt CH₂ *1 (D-47a) 4-005 3,5-Cl₂ CF₃CH₂SO₂CH₃ CH₂ *1 (D-47a) 4-006 3,5-Cl₂ CF₃ CH₂CH═CH₂ CH₂ *1 (D-47a)4-007 3,5-Cl₂ CF₃ CH(CH═CH₂)CH₂CH═CH₂ CH₂ *1 (D-47a) 4-008 3,5-Cl₂ CF₃CH₂Ph CH₂ *1 (D-47a) 4-009 3,5-Cl₂ CF₃ C(O)OCH₃ CH₂ *1 (D-47a) 4-0103,5-Cl₂ CF₃ Et CH₂ *1 (D-48e) Cl 4-011 3,5-Cl₂ CF₃ CH₃ OCH₃ *1

TABLE 11

No. (X)_(m) R³ (Y)_(n) R¹ m. p. (° C.) 5-001 3-Cl CF₃ 2-CH₃ CH₂(D-47a)*1 5-002 3-Br CF₃ 2-CH₃ CH₂CF₃ 158.5-161.0 5-003 3-Br CF₃ 2-CH₃CH₂(D-47a) *1 5-004 3-I CF₃ 2-CH₃ CH₂CF₃ 168.0-172.5 5-005 3-I CF₃ 2-CH₃CH₂(D-47a) 135.5-138.0 5-006 4-I CF₃ 2-CH₃ CH₂CF₃ 134.0-135.0 5-007 4-ICF₃ 2-CH₃ CH₂(D-47a) *1 5-008 3-CF₃ CF₃ 2-CH₃ CH₂CF₃ 135.5-137.5 5-0093-CF₃ CF₃ 2-CH₃ CH₂(D-47a) *1 5-010 3-(T-4) CF₃ 2-CH₃ CH₂CF₃ *2 5-0113-(T-4) CF₃ 2-CH₃ CH₂(D-47a) *2 5-012 3-OCF₃ CF₃ 2-CH₃ CH₂CF₃ *2 5-0133-OCF₃ CF₃ 2-CH₃ CH₂(D-47a) *1 5-014 3-OCF₂Br CF₃ 2-CH₃ CH₂CF₃ *1 5-0153-OCF₂Br CF₃ 2-CH₃ CH₂(D-47a) *2 5-016 3-OCF₂CHFOCF₂CF₂CF₃ CF₃ 2-CH₃CH₂CF₃ *1 5-017 3-OCF₂CHFOCF₂CF₂CF₃ CF₃ 2-CH₃ CH₂(D-47a) *1 5-0183-OCH₂(Ph-2-Cl) CF₃ 2-CH₃ CH₂(D-47a) *1 5-019 3-O[(D-47f)-3-Cl-5-CF₃]CF₃ 2-CH₃ CH₂CF₃ *1 5-020 3-O[(D-47f)-3-Cl-5-CF₃] CF₃ 2-CH₃ CH₂(D-47a)*1 5-021 3-SEt CF₃ 2-CH₃ CH₂(D-47a) *1 5-022 3-SCF₃ CF₃ 2-CH₃ CH₂CF₃ *15-023 3-SCF₃ CF₃ 2-CH₃ CH₂(D-47a) *1 5-024 3-N(CH₃)C(O)CF₃ CF₃ 2-CH₃CH₂CF₃ *1 5-025 3-N(CH₃)C(O)CF₃ CF₃ 2-CH₃ CH₂(D-47a) *1 5-0263-N(CH₃)SO₂CF₃ CF₃ 2-CH₃ CH₂CF₃ *1 5-027 3-N(CH₃)SO₂CF₃ CF₃ 2-CH₃CH₂(D-47a) *1 5-028 3-Ph CF₃ 2-CH₃ CH₂(D-47a) *1 5-029 3,5-F₂ CF₃ 2-CH₃CH₂(D-47a) *1 5-030 3,5-Cl₂ CH₃ 2-CH₃ CH₂CF₃ *1 5-031 3,5-Cl₂ i-Pr 2-CH₃CH₂CF₃ *1 5-032 3,5-Cl₂ c-Pr 2-CH₃ CH₂CF₃ 157.0-158.0 5-033 3,5-Cl₂ c-Pr2-CH₃ CH₂(D-47a) *1 5-034 3,5-Cl₂ CH₂Cl 2-CH₃ CH₂CF₃ 117.0-119.0 5-0353,5-Cl₂ CH₂Cl 2-CH₃ CH₂(D-47a) *1 5-036 3,5-Cl₂ CHF₂ 2-CH₃ CH₂CF₃94.0-97.5 5-037 3,5-Cl₂ CHF₂ 2-CH₃ CH₂(D-47a) *1 5-038 3,5-Cl₂ CF₃ 2-FCH₂CF₃ *1 5-039 3,5-Cl₂ CF₃ 2-F CH₂Ph 172.0-176.0 5-040 3,5-Cl₂ CF₃ 2-FCH₂(D-22a) *1 5-041 3,5-Cl₂ CF₃ 2-F CH₂(D-47a) 126.0-129.0 5-042 3,5-Cl₂CF₃ 3-F CH₂CF₃ *1 5-043 3,5-Cl₂ CF₃ 3-F CH₂Ph 178.0-181.0 5-044 3,5-Cl₂CF₃ 3-F CH₂(D-47a) 125.0-127.0 5-045 3,5-Cl₂ CF₃ 2-Cl CH₂Pr-c132.0-134.0 5-046 3,5-Cl₂ CF₃ 2-Cl CH₂CF₃ 124.0-125.0 5-047 3,5-Cl₂ CF₃2-Cl CH₂Ph 57.0-58.0 5-048 3,5-Cl₂ CF₃ 2-Cl CH₂(Ph-4-NO₂) *1 5-0493,5-Cl₂ CF₃ 2-Cl CH₂(D-21a) *1 5-050 3,5-Cl₂ CF₃ 2-Cl CH₂(D-22a) *15-051 3,5-Cl₂ CF₃ 2-Cl CH₂(D-22b)Cl *2 5-052 3,5-Cl₂ CF₃ 2-Cl CH₂(D-28a)*1 5-053 3,5-Cl₂ CF₃ 2-Cl CH₂(D-47a) *1 5-054 3,5-Cl₂ CF₃ 3-Cl CH₂CF₃149.0-150.0 5-055 3,5-Cl₂ CF₃ 3-Cl CH₂Ph 119.0-121.0 5-056 3,5-Cl₂ CF₃3-Cl CH₂(D-47a) *1 5-057 3,5-Cl₂ CF₃ 2-Br CH₂CF₃ 145.0-147.0 5-0583,5-Cl₂ CF₃ 2-Br CH₂(D-47a) *1 5-059 3,5-Cl₂ CF₃ 2-I CH₂CF₃ 128.0-130.05-060 3,5-Cl₂ CF₃ 2-I CH₂CH₂OEt *1 5-061 3,5-Cl₂ CF₃ 2-I CH₂CH(OCH₃)₂ *15-062 3,5-Cl₂ CF₃ 2-I CH₂C(O)NHCH₃ *1 5-063 3,5-Cl₂ CF₃ 2-ICH₂C(O)NHCH₂CH₂Cl 68.0-70.0 5-064 3,5-Cl₂ CF₃ 2-I CH₂CH═CH₂ 97.0-100.05-065 3,5-Cl₂ CF₃ 2-I CH₂(D-47a) *1 5-066 3,5-Cl₂ CF₃ 2-CH₃ H162.0-164.0 5-067 3,5-Cl₂ CF₃ 2-CH₃ Et 129.5-133.0 5-068 3,5-Cl₂ CF₃2-CH₃ c-Pr 84.0-86.0 5-069 3,5-Cl₂ CF₃ 2-CH₃ i-Bu 138.0-140.0 5-0703,5-Cl₂ CF₃ 2-CH₃ CH₂Pr-c *1 5-071 3,5-Cl₂ CF₃ 2-CH₃ c-Bu 139.0-141.05-072 3,5-Cl₂ CF₃ 2-CH₃ CH₂Bu-c *1 5-073 3,5-Cl₂ CF₃ 2-CH₃ c-Pen155.0-158.0 5-074 3,5-Cl₂ CF₃ 2-CH₃ CH₂CH₂Cl 161.5-164.5 5-075 3,5-Cl₂CF₃ 2-CH₃ CH₂CF₃ 155.5-157.0 5-075(+) 99% e. e. [α]_(D) ^(23.0) + 74.38°(EtOH, c = 0.621) *1 5-075(−) 99% e. e. [α]_(D) ^(22.8) − 70.98° (EtOH,c = 0.648) *1 5-076 3,5-Cl₂ CF₃ 2-CH₃ CH₂CH₂OCH₂ 115.0-117.0 5-0773,5-Cl₂ CF₃ 2-CH₃ CH₂CH₂OEt *1 5-078 3,5-Cl₂ CF₃ 2-CH₃ CH₂CH₂OCH₂CH₂Cl140.0-142.0 5-079 3,5-Cl₂ CF₃ 2-CH₃ CH₂CH₂OC(O)CH₃ *2 5-080 3,5-Cl₂ CF₃2-CH₃ CH₂CH₂OC(O)NHEt *2 5-081 3,5-Cl₂ CF₃ 2-CH₃ CH₂CH(CH₃)OH 67.0-70.05-082 3,5-Cl₂ CF₃ 2-CH₃ CH₂CH(CH₃)OCH₃ 179.0-181.0 5-083 3,5-Cl₂ CF₃2-CH₃ CH₂CH(OCH₃)₂ *1 5-084 3,5-Cl₂ CF₃ 2-CH₃ CH₂CH(OEt)₂ *2 5-0853,5-Cl₂ CF₃ 2-CH₃ CH(CH₃)CH₂OC(O)NHEt *1 5-086 3,5-Cl₂ CF₃ 2-CH₃CH₂(E-4a) *1 5-087 3,5-Cl₂ CF₃ 2-CH₃ CH₂(E-5a) *2 5-088 3,5-Cl₂ CF₃2-CH₃ CH₂(E-10a) 158.5-160.5 5-089 3,5-Cl₂ CF₃ 2-CH₃ CH₂(E-10b)CH₃153.0-154.0 5-090 3,5-Cl₂ CF₃ 2-CH₃ CH₂(E-32a) *1 5-091 3,5-Cl₂ CF₃2-CH₃ CH₂CH₂SCH₃ 121.0-127.0 5-092 3,5-Cl₂ CF₃ 2-CH₃ CH₂CH₂S(O)CH₃ *15-093 3,5-Cl₂ CF₃ 2-CH₃ CH₂CH₂SEt 106.0-109.0 5-094 3,5-Cl₂ CF₃ 2-CH₃CH₂CH₂SO₂Et *1 5-095 3,5-Cl₂ CF₃ 2-CH₃ CH₂CH₂SCH₂Ph *1 5-096 3,5-Cl₂ CF₃2-CH₃ CH₂CH₂SO₂CH₂Ph *1 5-097 3,5-Cl₂ CF₃ 2-CH₃ CH₂CH₂SCH₂(D-1a) *15-098 3,5-Cl₂ CF₃ 2-CH₃ CH₂CH₂SO₂CH₂(D-1a) *1 5-099 3,5-Cl₂ CF₃ 2-CH₃CH₂CH(CH₃)SCH₃ *1 5-100 3,5-Cl₂ CF₃ 2-CH₃ CH₂CH(CH₃)S(O)CH₃ *1 5-1013,5-Cl₂ CF₃ 2-CH₃ CH₂CH(CH₃)SO₂CH₃ *1 5-102 3,5-Cl₂ CF₃ 2-CH₃CH(CH₃)CH₂SCH₃ *1 5-103 3,5-Cl₂ CF₃ 2-CH₃ CH(CH₃)CH₂SO₂CH₃ *1 5-1043,5-Cl₂ CF₃ 2-CH₃ C(CH₃)₂CH₂SCH₃ *1 5-105 3,5-Cl₂ CF₃ 2-CH₃C(CH₃)₂CH₂SO₂CH₃ 167.0-169.0 5-106 3,5-Cl₂ CF₃ 2-CH₃ CH₂(E-18a)204.0-206.0 5-107 3,5-Cl₂ CF₃ 2-CH₃ CH₂(E-18c) 249.0-251.0 5-108 3,5-Cl₂CF₃ 2-CH₃ CH₂(E-43a) 199.0-201.0 5-109 3,5-Cl₂ CF₃ 2-CH₃ CH₂CH₂NHC(O)CF₃81.0-84.0 5-110 3,5-Cl₂ CF₃ 2-CH₃ CH₂CH₂NHC(O)CH₂CF₃ 143.0-146.0 5-1113,5-Cl₂ CF₃ 2-CH₃ CH₂C(O)CH₃ 155.0-160.0 5-112 3,5-Cl₂ CF₃ 2-CH₃CH₂CH═NOH *1 5-113 3,5-Cl₂ CF₃ 2-CH₃ CH₂CH═NOCH₃ *2 5-114 3,5-Cl₂ CF₃2-CH₃ CH₂CH═NOCH₂Pr-c *1 5-115 3,5-Cl₂ CF₃ 2-CH₃ CH₂CH═NOCH₂(Ph-4-Cl) *25-116 3,5-Cl₂ CF₃ 2-CH₃ CH₂CH═NOCH₂CH₂—TMS *1 5-117 3,5-Cl₂ CF₃ 2-CH₃CH₂C(CH₃)═NOCH₃ 101.0-105.0 5-118 3,5-Cl₂ CF₃ 2-CH₃ CH₂(M-5a)CH₃ *15-119 3,5-Cl₂ CF₃ 2-CH₃ CH₂CN 186.5-189.0 5-120 3,5-Cl₂ CF₃ 2-CH₃CH(OCH₂CF₃)CN *1 5-121 3,5-Cl₂ CF₃ 2-CH₃ CH(Ph)CN 165.5-167.0 5-1223,5-Cl₂ CF₃ 2-CH₃ CH(D-1a)CN *1 5-123 3,5-Cl₂ CF₃ 2-CH₃ CH(D-3a)CN *15-124 3,5-Cl₂ CF₃ 2-CH₃ CH(D-14a)CN 192.0-194.5 5-125 3,5-Cl₂ CF₃ 2-CH₃CH(D-38a)CN 185.0-189.5 5-126 3,5-Cl₂ CF₃ 2-CH₃ CH(D-47a)CN *1 5-1273,5-Cl₂ CF₃ 2-CH₃ CH₂C(O)OH 195.0-197.0 5-128 3,5-Cl₂ CF₃ 2-CH₃CH₂C(O)OCH₃ *2 5-129 3,5-Cl₂ CF₃ 2-CH₃ CH₂C(O)OCH₂CF₃ 157.0-158.0 5-1303,5-Cl₂ CF₃ 2-CH₃ CH(CH₃)C(O)OCH₃(D) *1 5-131 3,5-Cl₂ CF₃ 2-CH₃CH(CH₃)C(O)OEt(L) *1 5-132 3,5-Cl₂ CF₃ 2-CH₃ CH(CH₃)C(O)OCH₂CF₃ *1 5-1333,5-Cl₂ CF₃ 2-CH₃ CH(OH)C(O)OCH₃ *1 5-134 3,5-Cl₂ CF₃ 2-CH₃CH(OCH₃)C(O)OCH₃ *1 5-135 3,5-Cl₂ CF₃ 2-CH₃ CH(D-14a)C(O)OCH₃ 93.5-97.05-136 3,5-Cl₂ CF₃ 2-CH₃ CH₂CH₂C(O)OEt *1 5-137 3,5-Cl₂ CF₃ 2-CH₃CH₂C(O)NH₂ 87.0-91.0 5-138 3,5-Cl₂ CF₃ 2-CH₃ CH₂C(O)NHCH₃ *1 5-1393,5-Cl₂ CF₃ 2-CH₃ CH₂C(O)N(CH₃)₂ *1 5-140 3,5-Cl₂ CF₃ 2-CH₃ CH₂C(O)NHEt137.5-141.0 5-141 3,5-Cl₂ CF₃ 2-CH₃ CH₂C(O)NHPr-n *1 5-142 3,5-Cl₂ CF₃2-CH₃ CH₂C(O)NHPr-i 152.0-155.0 5-143 3,5-Cl₂ CF₃ 2-CH₃ CH₂C(O)NHBu-i *15-144 3,5-Cl₂ CF₃ 2-CH₃ CH₂C(O)NHBu-c 174.0-177.0 5-145 3,5-Cl₂ CF₃2-CH₃ CH₂C(O)NHBu-t *1 5-146 3,5-Cl₂ CF₃ 2-CH₃ CH₂C(O)NHCH₂Bu-t *1 5-1473,5-Cl₂ CF₃ 2-CH₃ CH₂C(O)NHCH₂CH₂F *1 5-148 3,5-Cl₂ CF₃ 2-CH₃CH₂C(O)NHCH₂CH₂Cl 109.0-112.0 5-149 3,5-Cl₂ CF₃ 2-CH₃CH₂C(O)N(CH₃)CH₂CH₂Cl *2 5-150 3,5-Cl₂ CF₃ 2-CH₃ CH₂C(O)NHCH₂CH₂Br *15-151 3,5-Cl₂ CF₃ 2-CH₃ CH₂C(O)NHCH₂CF₃ 173.5-175.5 5-151(+) 99% e. e.[α]_(D) ^(23.1) + 61.96° (EtOH, c = 1.098) *1 5-151(−) 99% e. e. [α]_(D)^(23.1) − 58.95° (EtOH, c = 1.153) *1 5-152 3,5-Cl₂ CF₃ 2-CH₃CH₂C(O)NHCH₂CH₂CH₂Cl *1 5-153 3,5-Cl₂ CF₃ 2-CH₃ CH₂C(O)NHCH₂(T-4) *15-154 3,5-Cl₂ CF₃ 2-CH₃ CH₂C(O)NHCH₂CH₂OH *1 5-155 3,5-Cl₂ CF₃ 2-CH₃CH₂C(O)N(CH₃)CH₂CH₂OH *1 5-156 3,5-Cl₂ CF₃ 2-CH₃ CH₂C(O)NHCH₂CH₂OCH₃146.0-149.0 5-157 3,5-Cl₂ CF₃ 2-CH₃ CH₂C(O)NHCH₂CH₂OEt *1 5-158 3,5-Cl₂CF₃ 2-CH₃ CH₂C(O)NHCH₂CH₂SCH₃ 138.0-143.0 5-159 3,5-Cl₂ CF₃ 2-CH₃CH₂C(O)NHCH₂CH₂SO₂CH₃ *1 5-160 3,5-Cl₂ CF₃ 2-CH₃ CH₂C(O)NHCH₂CH═CH₂76.0-79.0 5-161 3,5-Cl₂ CF₃ 2-CH₃ CH₂C(O)N(CH₃)CH₂CH═CH₂ *1 5-1623,5-Cl₂ CF₃ 2-CH₃ CH₂C(O)N(CH₂CH═CH₂)₂ *1 5-163 3,5-Cl₂ CF₃ 2-CH₃CH₂C(O)NHCH₂CCl═CH₂ *1 5-164 3,5-Cl₂ CF₃ 2-CH₃ CH₂C(O)NHCH₂CH═CCl₂188.0-192.0 5-165 3,5-Cl₂ CF₃ 2-CH₃ CH₂C(O)NHCH₂C≡CH *1 5-166 3,5-Cl₂CF₃ 2-CH₃ CH₂C(O)NHCH₂Ph 187.0-191.0 5-167 3,5-Cl₂ CF₃ 2-CH₃CH₂C(O)NHCH₂(D-22a) *1 5-168 3,5-Cl₂ CF₃ 2-CH₃ CH₂C(O)NHCH₂(D-47a) *15-169 3,5-Cl₂ CF₃ 2-CH₃ CH₂C(O)NHPh 181.0-183.0 5-170 3,5-Cl₂ CF₃ 2-CH₃CH₂C(O)(T-37) 118.0-121.0 5-171 3,5-Cl₂ CF₃ 2-CH₃ CH₂C(O)(T-40) *1 5-1723,5-Cl₂ CF₃ 2-CH₃ CH₂C(O)NHNHCH₂CF₃ 118.0-120.0 5-173 3,5-Cl₂ CF₃ 2-CH₃CH₂C(O)NHN(CH₃)Ph *1 5-174 3,5-Cl₂ CF₃ 2-CH₃ CH(CH₃)C(O)NHCH₂CH₂Cl146.0-149.0 5-175 3,5-Cl₂ CF₃ 2-CH₃ CH(Ph)C(O)NHCH₃(R) 118.0-121.0 5-1763,5-Cl₂ CF₃ 2-CH₃ CH(Ph)C(0)NHCH₃(S) *1 5-177 3,5-Cl₂ CF₃ 2-CH₃CH₂CH₂O(O)NHCH₂CH₂Cl 153.0-157.0 5-178 3,5-Cl₂ CF₃ 2-CH₃ CH₂(T-22) *15-179 3,5-Cl₂ CF₃ 2-CH₃ CH₂C(S)NH₂ *1 5-180 3,5-Cl₂ CF₃ 2-CH₃CH(Ph)C(S)NH₂ *1 5-181 3,5-Cl₂ CF₃ 2-CH₃ CH₂Si(CH₃)₃ *1 5-182 3,5-Cl₂CF₃ 2-CH₃ CH₂CH═CH₂ *1 5-183 3,5-Cl₂ CF₃ 2-CH₃ CH₂CCl═CH₂ *1 5-1843,5-Cl₂ CF₃ 2-CH₃ CH₂CH═CCl₂ *1 5-185 3,5-Cl₂ CF₃ 2-CH₃ CH₂CCl═CHCl *15-186 3,5-Cl₂ CF₃ 2-CH₃ CH₂C≡CH *1 5-187 3,5-Cl₂ CF₃ 2-CH₃ CH₂Ph142.0-144.5 5-188 3,5-Cl₂ CF₃ 2-CH₃ CH(CH₃)Ph 121.5-123.5 5-189 3,5-Cl₂CF₃ 2-CH₃ CH(CH₃)Ph(R) *1 5-189(+) 99% d. e. [α]_(D) ^(22.9) + 59.13°(EtOH, c = 0.262) *1 5-189(−) 99% d. e. [α]_(D) ^(23.0) − 86.72° (EtOH,c = 0.250) *1 5-190 3,5-Cl₂ CF₃ 2-CH₃ CH(CH₃)Ph(S) *1 5-190(+) 99% d. e.[α]_(D) ^(23.0) + 89.06° (EtOH, c = 0.466) *1 5-190(−) 99% d. e. [α]_(D)^(23.0) − 117.66° (EtOH, c = 0.322) *1 5-191 3,5-Cl₂ CF₃ 2-CH₃ CH(Et)Ph*1 5-192 3,5-Cl₂ CF₃ 2-CH₃ C(CH₃)₂Ph 91.0-93.5 5-193 3,5-Cl₂ CF₃ 2-CH₃CH(CF₃)Ph 175.5-180.0 5-194 3,5-Cl₂ CF₃ 2-CH₃ CH(OEt)Ph *2 5-195 3,5-Cl₂CF₃ 2-CH₃ CH₂(Ph-2-F) 151.0-153.0 5-196 3,5-Cl₂ CF₃ 2-CH₃ CH₂(Ph-3-F)134.0-136.0 5-197 3,5-Cl₂ CF₃ 2-CH₃ CH₂(Ph-4-F) 153.0-155.0 5-1983,5-Cl₂ CF₃ 2-CH₃ CH₂(Ph-2-Cl) 147.0-149.0 5-199 3,5-Cl₂ CF₃ 2-CH₃CH₂(Ph-3-Cl) 160.0-162.0 5-200 3,5-Cl₂ CF₃ 2-CH₃ CH₂(Ph-4-Cl)164.0-166.0 5-201 3,5-Cl₂ CF₃ 2-CH₃ CH₂(Ph-3-NO₂) 198.0-200.0 5-2023,5-Cl₂ CF₃ 2-CH₃ CH₂(Ph-4-NO₂) 204.0-206.0 5-203 3,5-Cl₂ CF₃ 2-CH₃CH₂(Ph-2,5-F₂) 153.0-155.0 5-204 3,5-Cl₂ CF₃ 2-CH₃ CH₂(Ph-3,5-F₂)146.0-149.0 5-205 3,5-Cl₂ CF₃ 2-CH₃ CH₂(D-1a) *1 5-206 3,5-Cl₂ CF₃ 2-CH₃CH₂(D-3a) 147.0-148.5 5-207 3,5-Cl₂ CF₃ 2-CH₃ CH₂(D-3d)Cl *1 5-2083,5-Cl₂ CF₃ 2-CH₃ CH₂(D-8b)CH₃ *1 5-209 3,5-Cl₂ CF₃ 2-CH₃ CH₂(D-10b)Cl*1 5-210 3,5-Cl₂ CF₃ 2-CH₃ CH₂(D-15a)CH₃ 147.0-148.0 5-211 3,5-Cl₂ CF₃2-CH₃ CH₂(D-16b)Cl 237.0-238.0 5-212 3,5-Cl₂ CF₃ 2-CH₃ CH₂(D-16c)Cl *15-213 3,5-Cl₂ CF₃ 2-CH₃ CH₂(D-16d) *1 5-214 3,5-Cl₂ CF₃ 2-CH₃CH₂(D-17a)CH₃ 76.0-77.0 5-215 3,5-Cl₂ CF₃ 2-CH₃ CH₂(D-17b)Cl 157.0-158.05-216 3,5-Cl₂ CF₃ 2-CH₃ CH₂(D-21a) *1 5-217 3,5-Cl₂ CF₃ 2-CH₃CH(Ph)(D-21a) *1 5-218 3,5-Cl₂ CF₃ 2-CH₃ CH₂(D-21b)CF₃ *1 5-219 3,5-Cl₂CF₃ 2-CH₃ CH₂(D-22a) 135.0-136.5 5-219(+) 97% e. e. [α]_(D) ^(22.6) +56.54° (EtOH, c = 0.384) *1 5-219(−) 99% e. e. [α]_(D) ^(22.4) − 58.65°(EtOH, c = 0.393) *1 5-220 3,5-Cl₂ CF₃ 2-CH₃ CH₂(D-22b)Cl *1 5-2213,5-Cl₂ CF₃ 2-CH₃ CH₂(D-22b)CH₃ *1 5-222 3,5-Cl₂ CF₃ 2-CH₃ CH₂(D-23a) *15-223 3,5-Cl₂ CF₃ 2-CH₃ CH₂(D-23b)Cl *1 5-224 3,5-Cl₂ CF₃ 2-CH₃CH₂(D-25a)CH₃ *1 5-225 3,5-Cl₂ CF₃ 2-CH₃ CH₂(D-27a)CH₃ *1 5-226 3,5-Cl₂CF₃ 2-CH₃ CH₂(D-28a) *1 5-227 3,5-Cl₂ CF₃ 2-CH₃ CH₂(D-29b)CH₃ *1 5-2283,5-Cl₂ CF₃ 2-CH₃ CH₂(D-30a) 120.0-123.5 5-229 3,5-Cl₂ CF₃ 2-CH₃CH₂(D-31a) 122.0-125.0 5-230 3,5-Cl₂ CF₃ 2-CH₃ CH₂(D-34a) *1 5-2313,5-Cl₂ CF₃ 2-CH₃ CH₂(D-34b)CH₃ *1 5-232 3,5-Cl₂ CF₃ 2-CH₃ CH₂(D-35a) *15-233 3,5-Cl₂ CF₃ 2-CH₃ CH₂(D-38a) *1 5-234 3,5-Cl₂ CF₃ 2-CH₃ CH₂(D-47a)131.0-135.5 5-235 3,5-Cl₂ CF₃ 2-CH₃ CH(CH₃)(D-47a) *1 5-236 3,5-Cl₂ CF₃2-CH₃ CH₂(D-47c)Cl 164.0-166.0 5-237 3,5-Cl₂ CF₃ 2-CH₃ CH₂(D-47c)NO₂129.0-131.0 5-238 3,5-Cl₂ CF₃ 2-CH₃ CH₂(D-47e)Cl *1 5-239 3,5-Cl₂ CF₃2-CH₃ CH₂(D-47i) *1 5-240 3,5-Cl₂ CF₃ 2-CH₃ CH₂(D-48a) *1 5-241 3,5-Cl₂CF₃ 2-CH₃ CH₂(D-48e)Cl 200.5-202.0 5-242 3,5-Cl₂ CF₃ 2-CH₃ CH₂(D-49a) *15-243 3,5-Cl₂ CF₃ 2-CH₃ CH₂(D-50a) *1 5-244 3,5-Cl₂ CF₃ 2-CH₃CH₂[(D-50d)-4,6-(OCH₃)₂] 58.0-65.0 5-245 3,5-Cl₂ CF₃ 2-CH₃ CH₂(D-51a) *15-246 3,5-Cl₂ CF₃ 2-CH₃ CH₂(D-53a) *1 5-247 3,5-Cl₂ CF₃ 2-CH₃CH₂(D-53b)CH₃ *1 5-248 3,5-Cl₂ CF₃ 2-CH₃ NH₂ 87.0-89.0 5-249 3,5-Cl₂ CF₃2-CH₃ N(CH₃)₂ 79.0-84.0 5-250 3,5-Cl₂ CF₃ 2-CH₃ NHBu-t 71.0-76.0 5-2513,5-Cl₂ CF₃ 2-CH₃ NHCH₂CF₃ 158.0-159.0 5-252 3,5-Cl₂ CF₃ 2-CH₃NHCH₂CH₂OH 61.0-70.0 5-253 3,5-Cl₂ CF₃ 2-CH₃ T-34a 59.0-63.0 5-2543,5-Cl₂ CF₃ 2-CH₃ T-40 95.0-105.0 5-255 3,5-Cl₂ CF₃ 2-CH₃ T-42155.0-157.0 5-256 3,5-Cl₂ CF₃ 2-CH₃ NHC(O)CH₃ 117.0-118.0 5-257 3,5-Cl₂CF₃ 2-CH₃ N(Ph)C(O)CH₃ 89.0-99.0 5-258 3,5-Cl₂ CF₃ 2-CH₃ NHC(O)Pr-n109.0-111.0 5-259 3,5-Cl₂ CF₃ 2-CH₃ NHC(O)CH₂CH₂Cl 109.0-110.0 5-2603,5-Cl₂ CF₃ 2-CH₃ NHC(O)CH₂CN 121.0-125.0 5-261 3,5-Cl₂ CF₃ 2-CH₃NHC(O)OCH₃ 86.0-93.0 5-262 3,5-Cl₂ CF₃ 2-CH₃ N(CH₃)C(O)OCH₃ 131.0-132.05-263 3,5-Cl₂ CF₃ 2-CH₃ N(Ph)C(O)OCH₃ 98.0-106.0 5-264 3,5-Cl₂ CF₃ 2-CH₃NHC(O)OEt 75.0-84.0 5-265 3,5-Cl₂ CF₃ 2-CH₃ NHC(O)OBu-t *1 5-266 3,5-Cl₂CF₃ 2-CH₃ NHC(O)OCH₂Ph 155.0-156.0 5-267 3,5-Cl₂ CF₃ 2-CH₃ NHC(O)NHPh212.0-214.0 5-268 3,5-Cl₂ CF₃ 2-CH₃ NHC(O)Ph 213.0-214.0 5-269 3,5-Cl₂CF₃ 2-CH₃ NHC(O)(D-1a) 230.0-232.0 5-270 3,5-Cl₂ CF₃ 2-CH₃ NHC(O)(D-47a)116.0-117.0 5-271 3,5-Cl₂ CF₃ 2-CH₃ NHC(S)NHCH₃ 143.0-145.0 5-2723,5-Cl₂ CF₃ 2-CH₃ NHC(S)N(CH₃)₂ 179.0-182.0 5-273 3,5-Cl₂ CF₃ 2-CH₃ NHPh88.0-96.0 5-274 3,5-Cl₂ CF₃ 2-CH₃ N(CH₃)Ph 158.0-160.0 5-275 3,5-Cl₂ CF₃2-CH₃ N(CH₂CH═CH₂)Ph 78.0-86.0 5-276 3,5-Cl₂ CF₃ 2-CH₃ N(CH₂Ph)Ph58.0-60.0 5-277 3,5-Cl₂ CF₃ 2-CH₃ NH(Ph-2-Cl) *1 5-278 3,5-Cl₂ CF₃ 2-CH₃NH(Ph-3-Cl) *1 5-279 3,5-Cl₂ CF₃ 2-CH₃ NH(Ph-4-Cl) *1 5-280 3,5-Cl₂ CF₃2-CH₃ NH(Ph-4-CF₃) *1 5-281 3,5-Cl₂ CF₃ 2-CH₃ NH(Ph-2-NO₂) 89.0-95.05-282 3,5-Cl₂ CF₃ 2-CH₃ NH(Ph-3-NO₂) 104.0-109.0 5-283 3,5-Cl₂ CF₃ 2-CH₃NH(Ph-4-NO₂) 120.0-126.0 5-284 3,5-Cl₂ CF₃ 2-CH₃ N(CH₃)(D-21a)181.0-185.0 5-285 3,5-Cl₂ CF₃ 2-CH₃ NH(D-47a) 213.0-217.0 5-286 3,5-Cl₂CF₃ 2-CH₃ N(CH₃)(D-47a) 202.0-203.0 5-287 3,5-Cl₂ CF₃ 2-CH₃ NH(D-47b)Cl102.0-103.0 5-288 3,5-Cl₂ CF₃ 2-CH₃ NH(D-47d)Cl 91.0-92.0 5-289 3,5-Cl₂CF₃ 2-CH₃ NH(D-47e)Cl 89.0-90.0 5-290 3,5-Cl₂ CF₃ 2-CH₃NH[(D-47f)-3-Cl-5-CF₃] 137.0-140.0 5-291 3,5-Cl₂ CF₃ 2-CH₃ NH(D-50a)209.0-211.0 5-292 3,5-Cl₂ CF₃ 2-CH₃ NH(D-50b)CF₃ 95.0-100.0 5-2933,5-Cl₂ CF₃ 2-CH₃ NH[(D-50d)-4,6-(OCH₃)₂] 91.0-98.0 5-294 3,5-Cl₂ CF₃2-CH₃ N(CH₃)(D-50a) 194.0-196.0 5-295 3,5-Cl₂ CF₃ 2-CH₃ N(Et)(D-50a)60.0-67.0 5-296 3,5-Cl₂ CF₃ 2-CH₃ NH(D-51b)SCH₃ *1 5-297 3,5-Cl₂ CF₃2-CH₃ NH(D-51b)S(O)CH₃ 156.0-162.0 5-298 3,5-Cl₂ CF₃ 2-CH₃NH(D-51b)SO₂CH₃ 147.0-151.0 5-299 3,5-Cl₂ CF₃ 2-CH₃ NH(D-51c)Cl *1 5-3003,5-Cl₂ CF₃ 2-CH₃ NH(D-53a) 111.0-112.0 5-301 3,5-Cl₂ CF₃ 2-CH₃NH(D-54b)Cl *1 5-302 3,5-Cl₂ CF₃ 2-CH₃ N═C(CH₃)Ph 134.0-135.0 5-3033,5-Cl₂ CF₃ 2-CH₃ N═CH(D-47a) *1 5-304 3,5-Cl₂ CF₃ 2-CH₃ T-47146.0-148.0 5-305 3,5-Cl₂ CF₃ 2-CH₃ D-8a 127.5-129.0 5-306 3,5-Cl₂ CF₃2-CH₃ (D-13b)CH₃ 271.0-275.0 5-307 3,5-Cl₂ CF₃ 2-CH₃ D-21a 281.0-284.05-308 3,5-Cl₂ CF₃ 2-CH₃ D-48a 188.0-190.0 5-309 3,5-Cl₂ CF₃ 2-CH₃ D-50a98.0-100.0 5-310 3,5-Cl₂ CF₃ 2-CH₃ D-51a 90.0-91.0 5-311 3,5-Cl₂ CF₃3-CH₃ CH₂CF₃ *1 5-312 3,5-Cl₂ CF₃ 2-Et CH₂CF₃ *1 5-313 3,5-Cl₂ CF₃ 2-EtCH₂(D-47a) *1 5-314 3,5-Cl₂ CF₃ 2-CF₃ CH₂CF₃ 70.0-72.0 5-315 3,5-Cl₂ CF₃2-CF₃ CH₂(D-47a) 69.0-70.0 5-316 3,5-Cl₂ CF₃ 2-CH₂OH CH₂CF₃ *1 5-3173,5-Cl₂ CF₃ 2-OCH₃ CH₂CF₃ *1 5-318 3,5-Cl₂ CF₃ 2-OCH₃ CH₂Ph *1 5-3193,5-Cl₂ CF₃ 2-OCH₃ CH₂(D-47a) 173.5-176.0 5-320 3,5-Cl₂ CF₃ 2-OCF₃CH₂CF₃ *2 5-321 3,5-Cl₂ CF₃ 2-OCF₃ CH₂(D-47a) 145.0-148.5 5-322 3,5-Cl₂CF₃ 2-SCH₃ CH₂CF₃ *2 5-323 3,5-Cl₂ CF₃ 2-SCH₃ CH₂(D-47a) *2 5-3243,5-Cl₂ CF₃ 2-S(O)CH₃ CH₂CF₃ *2 5-325 3,5-Cl₂ CF₃ 2-S(O)CH₃ CH₂(D-47a)*1 5-326 3,5-Cl₂ CF₃ 2-SO₂CH₃ CH₂CF₃ *1 5-327 3,5-Cl₂ CF₃ 2-SO₂CH₃CH₂(D-47a) 120.0-121.0 5-328 3,5-Cl₂ CF₃ 2-S(O)CH₂Cl CH₂CF₃ *2 5-3293,5-Cl₂ CF₃ 2-NH₂ CH₂CF₃ 78.0-79.0 5-330 3,5-Cl₂ CF₃ 2-NH₂ CH₂(D-47a) *25-331 3,5-Cl₂ CF₃ 2-NHCH₃ CH₂CF₃ 156.0-158.0 5-332 3,5-Cl₂ CF₃ 2-NHCH₃CH₂(D-47a) *1 5-333 3,5-Cl₂ CF₃ 2-NHC(O)CH₃ CH₂CF₃ *2 5-334 3,5-Cl₂ CF₃2-N(CH₃)₂ CH₂CF₃ *2 5-335 3,5-Cl₂ CF₃ 2-N(CH₃)2 CH₂(D-47a) *1 5-3363,5-Cl₂ CF₃ 2-N(CH₃)CHO CH₂(D-47a) *1 5-337 3,5-Cl₂ CF₃ 2-N(CH₃)C(O)CH₃CH₂(D-47a) *1 5-338 3,5-Cl₂ CF₃ 2-NO₂ CH₂CF₃ 180.0-181.0 5-339 3,5-Cl₂CF₃ 2-NO₂ CH₂(D-47a) *2 5-340 3,5-Cl₂ CF₃ 2-CN CH₂CF₃ *1 5-341 3,5-Cl₂CF₃ 2-CN CH₂(D-47a) *1 5-342 3,5-Cl₂ CF₃ 2-C≡C—TMS CH₂CF₃ *1 5-3433,5-Cl₂ CF₃ 2-Ph CH₂CF₃ *1 5-344 3,5-Cl₂ CF₃ 2-Ph CH₂(D-47a) 194.0-198.05-345 3,5-Cl₂ CF₃ 2-(D-38a) CH₂(D-47a) *2 5-346 3,5-Cl₂ CF₃ 2,3-F₂CH₂CF₃ *1 5-347 3,5-Cl₂ CF₃ 2,3-F₂ CH₂Ph *1 5-348 3,5-Cl₂ CF₃ 2,3-F₂CH₂(D-47a) *1 5-349 3,5-Cl₂ CF₃ 2,6-F₂ CH₂CF₃ 140.0-141.0 5-350 3,5-Cl₂CF₃ 2,6-Cl₂ CH₂(D-47a) 131.0-132.0 5-351 3,5-Cl₂ CF₃ 2,6-(CH₃)₂ CH₂CF₃125.0-129.0 5-352 3,5-Cl₂ CF₃ 2,6-(CH₃)₂ CH₂(D-47a) *1 5-353 3,5-Cl₂CF₂Cl 2-Cl CH₂(D-22a) *1 5-354 3,5-Cl₂ CF₂Cl 2-Cl CH₂(D-47a) *1 5-3553,5-Cl₂ CF₂Cl 2-CH₃ CH₂CF₃ *1 5-356 3,5-Cl₂ CF₂Cl 2-CH₃ CH₂CH₂OEt *15-357 3,5-Cl₂ CF₂Cl 2-CH₃ CH₂CH(OCH₃)₂ *1 5-358 3,5-Cl₂ CF₂Cl 2-CH₃CH₂CH═CH₂ *1 5-359 3,5-Cl₂ CF₂Cl 2-CH₃ CH₂(D-22a) *1 5-360 3,5-Cl₂ CF₂Cl2-CH₃ CH₂(D-47a) *1 5-361 3,5-Cl₂ CF₂CF₃ 2-CH₃ CH₂CF₃ *1 5-362 3,5-Cl₂CF₂CF₃ 2-CH₃ CH₂(D-47a) *1 5-363 3,5-Cl₂ CF₂CF₃ 2-CH₃ C(O)(D-47a) *15-364 3,5-Cl₂ CH₂OCH₂CF₃ 2-CH₃ CH₂CF₃ *1 5-365 3,5-Cl₂ CH₂OCH₂CF₃ 2-CH₃CH₂(D-47a) *1 5-366 3,5-Cl₂ CF₂SCH₃ 2-CH₃ CH₂CF₃ *2 5-367 3,5-Cl₂CF₂SCH₃ 2-CH₃ CH₂(D-47a) 51.0-52.0 5-368 3,5-Cl₂ CH₂—TMS 2-CH₃ CH₂CF₃ *15-369 3,5-Cl₂ CH₂—TMS 2-CH₃ CH₂(D-47a) *1 5-370 3,5-Cl₂ TMS 2-CH₃ CH₂CF₃*1 5-371 3,5-Cl₂ TMS 2-CH₃ CH₂(D-47a) *1 5-372 3,5-Cl₂ D-47a 2-CH₃CH₂CF₃ *1 5-373 3,5-Cl₂ D-47a 2-CH₃ CH₂(D-47a) *1 5-374 3-Cl-5-Br CF₃2-CH₃ CH₂CF₃ *1 5-375 3-Cl-5-Br CF₃ 2-CH₃ CH₂(D-47a) *1 5-376 3,5-Br₂CF₃ 2-Cl CH₂(D-22a) 63.0-64.0 5-377 3,5-Br₂ CF₃ 2-Cl CH₂(D-47a) *2 5-3783,5-Br₂ CF₃ 2-CH₃ CH₂CF₃ *1 5-379 3,5-Br₂ CF₃ 2-CH₃ CH₂CH₂OCH₃ *2 5-3803,5-Br₂ CF₃ 2-CH₃ CH₂CH₂OEt *2 5-381 3,5-Br₂ CF₃ 2-CH₃ CH₂CH(OCH₃)₂ *25-382 3,5-Br₂ CF₃ 2-CH₃ CH₂C(O)OCH₃ *2 5-383 3,5-Br₂ CF₃ 2-CH₃CH₂C(O)NHCH₂CH₂Cl 69.0-70.0 5-384 3,5-Br₂ CF₃ 2-CH₃ CH₂C(O)NHCH₂CF₃173.0-175.0 5-385 3,5-Br₂ CF₃ 2-CH₃ CH₂CH═CH₂ *2 5-386 3,5-Br₂ CF₃ 2-CH₃CH₂(D-22a) *1 5-387 3,5-Br₂ CF₃ 2-CH₃ CH₂(D-47a) *1 5-388 3-Cl-5-CH₃ CF₃2-CH₃ CH₂(D-47a) *2 5-389 3,5-(CF₃)₂ CF₃ 2-CH₃ CH₂CF₃ *1 5-3903,5-(CF₃)₂ CF₃ 2-CH₃ CH₂(D-47a) *1 5-391 3-F-5-SCH₃ CF₃ 2-CH₃ CH₂(D-47a)*1 5-392 3-Cl-5-SCH₃ CF₃ 2-SCH₃ CH₂(D-47a) *2 5-393 3-CF₃-5-OCH₃ CF₃2-CH₃ CH₂(D-47a) *1 5-394 3,5-(SCH₃)₂ CF₃ 2-CH₃ CH₂(D-47a) *1 5-3953-CF₃-5-CN CF₃ 2-CH₃ CH₂CF₃ 72.0-73.0 5-396 3-CF₃-5-CN CF₃ 2-CH₃CH₂(D-47a) 63.0-64.0 5-397 3,4,5-Cl₃ CF₃ 2-CH₃ CH₂CF₃ 194.0-197.0 5-3983,4,5-Cl₃ CF₃ 2-CH₃ CH₂(D-47a) *1 5-399 3,5-Cl₂ CF₃ 2-CH₃ CH₂CH₂CF₃ *15-400 3,5-Cl₂ CF₃ 2-CH₃ CH(CF₃)OH *1 5-401 3,5-Cl₂ CF₃ 2-CH₃ CH(CF₃)OCH₃*1 5-402 3,5-Cl₂ CF₃ 2-CH₃ E-5b 197.0-199.0 5-403 3,5-Cl₂ CF₃ 2-CH₃CH₂CH₂(T-33) *1 5-404 3,5-Cl₂ CF₃ 2-CH₃ CH₂CH₂(T-39) *1 5-405 3,5-Cl₂CF₃ 2-CH₃ (E-9b)CH₂CF₃ *2 5-406 3,5-Cl₂ CF₃ 2-CH₃ CH₂(E-17a)H *1 5-4073,5-Cl₂ CF₃ 2-CH₃ CH[C(O)OCH₃]₂ *2 5-408 3,5-Cl₂ CF₃ 2-CH₃ CH₂C(O)NHOEt141.0-145.0 5-409 3,5-Cl₂ CF₃ 2-CH₃ CH₂C(O)NHOCH₂CH═CH₂ *1 5-410 3,5-Cl₂CF₃ 2-CH₃ CH(CH₃)C(O)NHEt *1 5-411 3,5-Cl₂ CF₃ 2-CH₃ CH(CH₃)C(O)NHPr-i172.0-174.0 5-412 3,5-Cl₂ CF₃ 2-CH₃ CH(CH₃)C(O)NHCH₂CF₃ 161.0-163.05-413 3,5-Cl₂ CF₃ 2-CH₃ CH(CH₃)C(O)NHCH₂CH═CH₂ 175.0-178.0 5-414 3,5-Cl₂CF₃ 2-CH₃ T-48 *2 5-415 3,5-Cl₂ CF₃ 2-CH₃ T-49 *2 5-416 3,5-Cl₂ CF₃2-CH₃ CH[C(O)NHCH₃]₂ 146.0-149.0 5-417 3,5-Cl₂ CF₃ 2-CH₃ CH(OCH₃)Ph *15-418 3,5-Cl₂ CF₃ 2-CH₃ CH(CH₃)(D-1a) 142.0-144.0 5-419 3,5-Cl₂ CF₃2-CH₃ CH₂(D-6a)CH₃ 155.0-157.0 5-420 3,5-Cl₂ CF₃ 2-CH₃ CH(CF₃)(D-6a)H *15-421 3,5-Cl₂ CF₃ 2-CH₃ CH₂(D-11a) *1 5-422 3,5-Cl₂ CF₃ 2-CH₃CH(CF₃)(D-14a) 114.0-118.0 5-423 3,5-Cl₂ CF₃ 2-CH₃ CH(CH₃)(D-21a) *25-424 3,5-Cl₂ CF₃ 2-CH₃ CH(CF₃)(D-24a) *1 5-425 3,5-Cl₂ CF₃ 2-CH₃CH₂(D-26a)CH₃ *1 5-426 3,5-Cl₂ CF₃ 2-CH₃ CH(CH₃)(D-38a) *1 5-427 3,5-Cl₂CF₃ 2-CH₃ CH(CF₃)(D-38a) *1 5-428 3,5-Cl₂ CF₃ 2-CH₃ C(O)OCH₂CF₃ *1 5-4293,5-Cl₂ CF₃ 2-CH₃ C(O)NHCH₂CF₃ 81.5-83.0 5-430 3,5-Cl₂ CF₃ 2-CH₃C(S)NHCH₂CF₃ 137.5-140.0 5-431 3,5-Cl₂ CF₃ 2-CH₃ C(D-49a)═C(CN)₂122.0-124.0 5-432 3,5-Cl₂ CF₃ 2-CH₃ NHC(O)NHCH₂CH₂Cl 105.0-108.0 5-4333,5-Cl₂ CF₃ 2-CH₃ N(CH₂C≡CH)Ph 76.0-84.0 5-434 3,5-Cl₂ CF₃ 2-CH₃ Ph-4-CN*1 5-435 3,5-Cl₂ CF₃ 2-CH₃ Ph-4-C(O)OH 248.0-251.0 5-436 3,5-Cl₂ CF₃2-CH₃ Ph-4-C(O)OEt 230.0-232.0 5-437 3,5-Cl₂ CF₃ 2-CH₃Ph-4-C(O)NHCH₂CH₂Cl 188.0-195.0 5-438 3,5-Cl₂ CF₃ 2-CH₃Ph-4-C(O)NHCH₂CF₃ 110.0-120.0 5-439 3,5-Cl₂ CF₃ 2-CH₃ (D-8b)CH₃163.0-165.0 5-440 3,5-Cl₂ CF₃ 2-CH₃ (D-15a)CH₃ 96.0-110.0 5-441 3,5-Cl₂CF₃ 2-CH₃ (D-17a)CH₃ 95.0-101.0 5-442 3,5-Cl₂ CF₃ 2-CH₃ (D-17b)Cl100.0-108.0 5-443 3,5-Cl₂ CF₃ 2-CH₃ (D-21b)CH₃ 110.0-114.0 5-444 3,5-Cl₂CF₃ 2-CH₃ (D-21c)Cl 288.0-292.0 5-445 3,5-Cl₂ CF₃ 2-CH₃ (D-21c)CH₃271.0-273.0 5-446 3,5-Cl₂ CF₃ 2-CH₃ D-35a 117.0-126.0 5-447 3,5-Cl₂ CF₃2-CH₃ (D-35b)CH₃ 227.0-230.0 5-448 3,5-Cl₂ CF₃ 2-CH₃ (D-39c)SCH₃188.0-190.0 5-449 3,5-Cl₂ CF₃ 2-CH₃ (D-42a)H 109.0-112.0 5-450 3,5-Cl₂CH(OEt)₂ 2-CH₃ CH₂(D-47a) *1 5-451 3,5-Br₂ CF₃ 2-CH₃ CH₂C(O)OH102.0-106.0 5-452 3-CF₃-5-NO₂ CF₃ 2-CH₃ CH₂CF₃ *1 5-453 3-CF₃-5-NO₂ CF₃2-CH₃ CH₂(D-47a) *1 5-454 3,5-Cl₂-4-NH₂ CF₃ 2-CH₃ CH₂CF₃ 153.0-154.05-455 3,5-Cl₂-4-NH₂ CF₃ 2-CH₃ CH₂(D-47a) *1 5-456 3,5-Cl₂-4-NHC(O)OBu-tCF₃ 2-CH₃ CH₂CF₃ *1 5-457 3,5-Cl₂-4-NHC(O)OBu-t CF₃ 2-CH₃ CH₂(D-47a) *15-458 3,4-Cl₂ CF₃ 2-CH₃ CH₂CF₃ 138.0-140.0 5-459 3,4-Cl₂ CF₃ 2-CH₃CH₂C(O)NHCH₂CF₃ 165.0-167.0 5-460 3,4-Cl₂ CF₃ 2-CH₃ CH₂(D-22a) *2 5-4613,4-Cl₂ CF₃ 2-CH₃ CH₂(D-47a) *2 5-462 3,5-Cl₂ CF₃ 2-Cl H *1 5-4633,5-Cl₂ CF₃ 2-Cl CH₂C(O)NHCH₂CF₃ *1 5-464 3,5-Cl₂ CF₃ 2-Cl (D-50c)Cl115.0-117.0 5-465 3,5-Cl₂ CF₃ 2-Br CH₂C(O)NHCH₂CF₃ 159.0-163.0 5-4663,5-Cl₂ CF₃ 2-Br (D-57d)Cl 172.0-174.0 5-467 3,5-Cl₂ CF₃ 2-I H126.0-128.0 5-468 3,5-Cl₂ CF₃ 2-I CH₂C(O)NHCH₂CF₃ *1 5-469 3,5-Cl₂ CF₃2-I (D-47d)Cl 125.0-128.0 5-470 3,5-Cl₂ CF₃ 2-I (D-50c)Cl *1 5-4713,5-Cl₂ CF₃ 2-CH₃ CH₃ *1 5-472 3,5-Cl₂ CF₃ 2-CH₃ CH₂CHF₂ *1 5-4733,5-Cl₂ CF₃ 2-CH₃ CH₂OCH₃ *1 5-474 3,5-Cl₂ CF₃ 2-CH₃ CH₂OEt *1 5-4753,5-Cl₂ CF₃ 2-CH₃ CH₂OPr-n *1 5-476 3,5-Cl₂ CF₃ 2-CH₃ CH₂OPr-i *1 5-4773,5-Cl₂ CF₃ 2-CH₃ CH₂OCH₂CH₂Cl *1 5-478 3,5-Cl₂ CF₃ 2-CH₃ CH₂OCH₂CHF₂ *15-479 3,5-Cl₂ CF₃ 2-CH₃ CH₂OCH₂CHCl₂ *1 5-480 3,5-Cl₂ CF₃ 2-CH₃CH₂OCH₂CF₃ 111.0-114.0 5-481 3,5-Cl₂ CF₃ 2-CH₃ CH₂OCH₂CCl₃ *1 5-4823,5-Cl₂ CF₃ 2-CH₃ CH₂OCH₂CH₂OCH₃ *1 5-483 3,5-Cl₂ CF₃ 2-CH₃CH₂OCH₂CH═CH₂ *1 5-484 3,5-Cl₂ CF₃ 2-CH₃ CH₂OCH₂C≡CH *1 5-485 3,5-Cl₂CF₃ 2-CH₃ CH₂OCH₂Ph *1 5-486 3,5-Cl₂ CF₃ 2-CH₃ CH₂OC(O)CH₃ *1 5-4873,5-Cl₂ CF₃ 2-CH₃ CH(CH₃)OH *1 5-488 3,5-Cl₂ CF₃ 2-CH₃ CH(CH₃)OCH₂CF₃ *15-489 3,5-Cl₂ CF₃ 2-CH₃ CH₂CH₂OCH₂CF₃ 156.0-159.0 5-490 3,5-Cl₂ CF₃2-CH₃ CH₂CH₂OCH₂CH₂OCH₂CH₂OCH₃ *2 5-491 3,5-Cl₂ CF₃ 2-CH₃ CH(CH₃)CH₂OH160.0-164.0 5-492 3,5-Cl₂ CF₃ 2-CH₃ CH(CH₃)CH₂OC(O)CH₃ *1 5-493 3,5-Cl₂CF₃ 2-CH₃ CH(CH₃)CH₂OC(O)NHCH₂CH₂Cl *1 5-494 3,5-Cl₂ CF₃ 2-CH₃ E-4a144.0-147.0 5-495 3,5-Cl₂ CF₃ 2-CH₃ E-5a(R) *1 5-496 3,5-Cl₂ CF₃ 2-CH₃E-23a *1 5-497 3,5-Cl₂ CF₃ 2-CH₃ CH₂SCH₃ *1 5-498 3,5-Cl₂ CF₃ 2-CH₃CH₂S(O)CH₃ 159.0-161.0 5-499 3,5-Cl₂ CF₃ 2-CH₃ CH₂SO₂CH₃ 207.0-209.05-500 3,5-Cl₂ CF₃ 2-CH₃ CH₂SC(O)CH₃ *1 5-501 3,5-Cl₂ CF₃ 2-CH₃CH₂SC(S)OEt *1 5-502 3,5-Cl₂ CF₃ 2-CH₃ CH₂SO₂OH•Q5 *1 5-503 3,5-Cl₂ CF₃2-CH₃ CH₂CH₂SC(O)NHEt 148.0-150.0 5-504 3,5-Cl₂ CF₃ 2-CH₃CH₂CH₂SC(O)NH(Ph-4-F) *2 5-505 3,5-Cl₂ CF₃ 2-CH₃ CH₂CH₂S(D-50a) *2 5-5063,5-Cl₂ CF₃ 2-CH₃ CH₂CH₂SO₂(D-50a) *2 5-507 3,5-Cl₂ CF₃ 2-CH₃ CH₂NH₂•Q1155.0-157.0 5-508 3,5-Cl₂ CF₃ 2-CH₃ CH₂NHEt *1 5-509 3,5-Cl₂ CF₃ 2-CH₃CH₂NHCH₂CF₃ *1 5-510 3,5-Cl₂ CF₃ 2-CH₃ CH₂N(CH₂CF₃)C(O)CH₃ *1 5-5113,5-Cl₂ CF₃ 2-CH₃ CH₂N(CH₂CF₃)C(O)OCH₃ *1 5-512 3,5-Cl₂ CF₃ 2-CH₃CH₂NHC(O)CH₃ 112.0-114.0 5-513 3,5-Cl₂ CF₃ 2-CH₃ CH₂NHC(O)CF₃191.0-194.0 5-514 3,5-Cl₂ CF₃ 2-CH₃ CH₂NHC(O)CH₂CF₃ 212.0-217.0 5-5153,5-Cl₂ CF₃ 2-CH₃ CH₂NHC(O)OCH₃ *1 5-516 3,5-Cl₂ CF₃ 2-CH₃ CH₂NHC(O)OEt110.0-120.0 5-517 3,5-Cl₂ CF₃ 2-CH₃ CH₂NHC(O)OCH₂CF₃ 118.0-119.0 5-5183,5-Cl₂ CF₃ 2-CH₃ CH₂NHC(O)NHEt 152.0-154.0 5-519 3,5-Cl₂ CF₃ 2-CH₃CH(CH₃)NHC(O)OCH₃ 88.0-90.0 5-520 3,5-Cl₂ CF₃ 2-CH₃CH₂CH₂NHC(O)OCH₂CH₂Cl 96.0-99.0 5-521 3,5-Cl₂ CF₃ 2-CH₃ CH₂CH₂NHSO₂Et *15-522 3,5-Cl₂ CF₃ 2-CH₃ CH₂CH═NOCH₂CF₃ *1 5-523 3,5-Cl₂ CF₃ 2-CH₃CH(CH₃)CH═NOCH₃ *1 5-524 3,5-Cl₂ CF₃ 2-CH₃ CH(CH₂OH)C(O)OCH₃ *1 5-5253,5-Cl₂ CF₃ 2-CH₃ CH₂CH₂CH₂C(O)OEt *1 5-526 3,5-Cl₂ CF₃ 2-CH₃ E-7e192.0-194.5 5-527 3,5-Cl₂ CF₃ 2-CH₃ CH₂C(O)N(CH₃)Et *1 5-528 3,5-Cl₂ CF₃2-CH₃ CH₂C(O)N(Et)₂ *1 5-529 3,5-Cl₂ CF₃ 2-CH₃ CH₂C(O)NHPr-c 146.0-147.05-530 3,5-Cl₂ CF₃ 2-CH₃ CH₂C(O)NHBu-s 148.0-149.0 5-531 3,5-Cl₂ CF₃2-CH₃ CH₂C(O)NHCH₂Pr-c 195.0-197.0 5-532 3,5-Cl₂ CF₃ 2-CH₃CH₂C(O)NHCH₂CH(OEt)₂ *1 5-533 3,5-Cl₂ CF₃ 2-CH₃ CH₂C(O)NHCH₂CN198.0-201.0 5-534 3,5-Cl₂ CF₃ 2-CH₃ CH₂C(O)NHCH₂C(O)NHCH₃ 170.0-172.05-535 3,5-Cl₂ CF₃ 2-CH₃ CH₂C(O)NHCH₂C(O)NHCH₂CF3 180.0-183.0 5-5363,5-Cl₂ CF₃ 2-CH₃ CH₂C(O)NH(Ph-4-F) 235.0-237.0 5-537 3,5-Cl₂ CF₃ 2-CH₃CH₂C(O)NH(Ph-4-CN) 267.0-269.0 5-538 3,5-Cl₂ CF₃ 2-CH₃ CH(CH₃)C(O)NH₂ *15-539 3,5-Cl₂ CF₃ 2-CH₃ CH(CH₃)C(O)NHCH₂CH₂Cl(D) 162.0-164.0 5-5403,5-Cl₂ CF₃ 2-CH₃ CH(CH₃)C(0)NHCH₂CH₂Cl(L) 149.0-151.0 5-540(+) 99% d.e. [α]_(D) ^(22.9) + 54.77° (EtOH, c = 0.652) 103.0-105.0 5-541 3,5-Cl₂CF₃ 2-CH₃ CH(CH₃)C(O)NHCH₂CF₃(D) 188.0-190.0 [α]_(D) ^(24.7) + 14.89°(EtOH, c = 0.744) 5-541(R) 95% d. e. [α]_(D) ^(24.9) − 54.42° (EtOH, c =0.890) 164.0-166.0 5-541(S) 95% d. e. [α]_(D) ^(24.9) + 50.27° (EtOH, c= 0.650) 216.0-217.0 5-542 3,5-Cl₂ CF₃ 2-CH₃ CH(CH₃)C(O)NHCH₂CF₃(L)181.0-183.0 5-543 3,5-Cl₂ CF₃ 2-CH₃ CH(Et)C(O)NHCH₂CF₃ 197.0-205.0 5-5443,5-Cl₂ CF₃ 2-CH₃ CH(Pr-i)C(O)NHCH₂CF₃ 220.0-224.0 5-545 3,5-Cl₂ CF₃2-CH₃ CH₂CH₂CH₂C(O)NHCH₂CF₃ 172.0-175.0 5-546 3,5-Cl₂ CF₃ 2-CH₃ T-50 *25-547 3,5-Cl₂ CF₃ 2-CH₃ T-51 *2 5-548 3,5-Cl₂ CF₃ 2-CH₃ CH₂(D-14b)CF₃ *15-549 3,5-Cl₂ CF₃ 2-CH₃ CH₂(D-17b)CF₃ 219.0-222.0 5-550 3,5-Cl₂ CF₃2-CH₃ CH₂(D-21e) 71.0-79.0 5-551 3,5-Cl₂ CF₃ 2-CH₃ CH₂(D-22a)•Q1177.0-177.5 5-552 3,5-Cl₂ CF₃ 2-CH₃ CH₂(D-22a)•Q2 95.0-103.0 5-5533,5-Cl₂ CF₃ 2-CH₃ CH₂(D-22a)•Q3 135.0-137.0 5-554 3,5-Cl₂ CF₃ 2-CH₃CH₂(D-22a)•Q4 125.0-130.0 5-555 3,5-Cl₂ CF₃ 2-CH₃ CH₂(D-22b)SCH₃ *15-556 3,5-Cl₂ CF₃ 2-CH₃ CH₂(D-22b)SO₂CH₃ *1 5-557 3,5-Cl₂ CF₃ 2-CH₃CH₂(D-22b)CF₃ *1 5-558 3,5-Cl₂ CF₃ 2-CH₃ CH₂(D-37a) *2 5-559 3,5-Cl₂ CF₃2-CH₃ CH₂(D-61b) *1 5-560 3,5-Cl₂ CF₃ 2-CH₃ CH(CH₃)(D-14a) *1 5-5613,5-Cl₂ CF₃ 2-CH₃ OCH₃ *1 5-562 3,5-Cl₂ CF₃ 2-CH₃ OCH₂CH═CH₂ 158.0-160.05-563 3,5-Cl₂ CF₃ 2-CH₃ SO₂CH₃ *1 5-564 3,5-Cl₂ CF₃ 2-CH₃ SO₂N(CH₃)₂ *25-565 3,5-Cl₂ CF₃ 2-CH₃ N(Ph)C(O)CH₂Cl *1 5-566 3,5-Cl₂ CF₃ 2-CH₃N═CHN(CH₃)₂ 100.0-106.0 5-567 3,5-Cl₂ CF₃ 2-CH₃ N═C(CH₃)N(CH₃)₂79.0-84.0 5-568 3,5-Cl₂ CF₃ 2-CH₃ CHO 179.0-181.0 5-569 3,5-Cl₂ CF₃2-CH₃ C(O)CH₂CF₃ 148.0-150.0 5-570 3,5-Cl₂ CF₃ 2-CH₃ C(O)OCH₂CH₂F144.0-146.0 5-571 3,5-Cl₂ CF₃ 2-CH₃ C(O)OCH₂CHF₂ 165.0-168.0 5-5723,5-Cl₂ CF₃ 2-CH₃ C(O)OCH(CH₂F)₂ *1 5-573 3,5-Cl₂ CF₃ 2-CH₃C(O)OCH(CH₂F)CH₂Cl *1 5-574 3,5-Cl₂ CF₃ 2-CH₃ C(O)NHCH₃ 161.0-163.05-575 3,5-Cl₂ CF₃ 2-CH₃ C(O)N(CH₃)₂ *2 5-576 3,5-Cl₂ CF₃ 2-CH₃ C(O)NHEt178.0-180.0 5-577 3,5-Cl₂ CF₃ 2-CH₃ C(O)NHCH₂CH₂Cl 210.0-213.0 5-5783,5-Cl₂ CF₃ 2-CH₃ C(O)NHCH₂C(O)NHCH₂CF₃ 231.0-232.0 5-579 3,5-Cl₂ CF₃2-CH₃ C(O)NHCH₂CH═CH₂ 160.0-162.0 5-580 3,5-Cl₂ CF₃ 2-CH₃C(O)NHCH₂(Ph-4-F) 101.0-104.0 5-581 3,5-Cl₂ CF₃ 2-CH₃ C(O)NHCH₂(D-47a)*1 5-582 3,5-Cl₂ CF₃ 2-CH₃ C(O)NH(Ph-4-F) 188.0-191.0 5-583 3,5-Cl₂ CF₃2-CH₃ C(O)(T-33) *2 5-584 3,5-Cl₂ CF₃ 2-CH₃ C(S)NHCH₃ 98.0-101.0 5-5853,5-Cl₂ CF₃ 2-CH₃ Ph *1 5-586 3,5-Cl₂ CF₃ 2-CH₃ Ph-2-F 164.0-167.0 5-5873,5-Cl₂ CF₃ 2-CH₃ Ph-3-F 163.0-171.0 5-588 3,5-Cl₂ CF₃ 2-CH₃ Ph-4-F *15-589 3,5-Cl₂ CF₃ 2-CH₃ Ph-4-Cl 165.0-169.0 5-590 3,5-Cl₂ CF₃ 2-CH₃Ph-4-CF₃ 95.0-99.0 5-591 3,5-Cl₂ CF₃ 2-CH₃ Ph-2-OH *1 5-592 3,5-Cl₂ CF₃2-CH₃ Ph-4-OCH₃ 180.0-182.0 5-593 3,5-Cl₂ CF₃ 2-CH₃ Ph-4-OCF₃165.0-167.0 5-594 3,5-Cl₂ CF₃ 2-CH₃ Ph-4-OSO₂CH₃ 160.0-163.0 5-5953,5-Cl₂ CF₃ 2-CH₃ Ph-4-SCH₃ 181.0-183.0 5-596 3,5-Cl₂ CF₃ 2-CH₃Ph-4-S(O)CH₃ 119.0-126.0 5-597 3,5-Cl₂ CF₃ 2-CH₃ Ph-4-SO₂CH₃ 222.0-225.05-598 3,5-Cl₂ CF₃ 2-CH₃ Ph-4-SO₂NH₂ 126.0-130.0 5-599 3,5-Cl₂ CF₃ 2-CH₃Ph-4-NO₂ 141.0-148.0 5-600 3,5-Cl₂ CF₃ 2-CH₃ Ph-2-CN 168.0-175.0 5-6013,5-Cl₂ CF₃ 2-CH₃ Ph-3-CN *1 5-602 3,5-Cl₂ CF₃ 2-CH₃ Ph-4-C(O)NH₂209.0-213.0 5-603 3,5-Cl₂ CF₃ 2-CH₃ Ph-2-C(O)NHPr-i *1 5-604 3,5-Cl₂ CF₃2-CH₃ Ph-2,4-F₂ *1 5-605 3,5-Cl₂ CF₃ 2-CH₃ Ph-2,5-F₂ *1 5-606 3,5-Cl₂CF₃ 2-CH₃ Ph-2,6-F₂ 177.5-181.0 5-607 3,5-Cl₂ CF₃ 2-CH₃ Ph-3,4-F₂154.0-160.0 5-608 3,5-Cl₂ CF₃ 2-CH₃ Ph-2-F-4-Cl 140.0-142.0 5-6093,5-Cl₂ CF₃ 2-CH₃ Ph-3,4-Cl₂ *1 5-610 3,5-Cl₂ CF₃ 2-CH₃ Ph-3,5-Cl₂ *15-611 3,5-Cl₂ CF₃ 2-CH₃ Ph-3-NO₂-4-F *1 5-612 3,5-Cl₂ CF₃ 2-CH₃Ph-2,4,6-F₃ *1 5-613 3,5-Cl₂ CF₃ 2-CH₃ Ph-2,6-F₂-4-Br 215.0-217.0 5-6143,5-Cl₂ CF₃ 2-CH₃ D-3a 102.0-107.0 5-615 3,5-Cl₂ CF₃ 2-CH₃ D-5a *1 5-6163,5-Cl₂ CF₃ 2-CH₃ (D-10b)CH₃ 190.0-193.0 5-617 3,5-Cl₂ CF₃ 2-CH₃ D-14a*1 5-618 3,5-Cl₂ CF₃ 2-CH₃ (D-14c)Br *1 5-619 3,5-Cl₂ CF₃ 2-CH₃(D-21b)CF₃ *1 5-620 3,5-Cl₂ CF₃ 2-CH₃ D-21e 182.0-187.0 5-621 3,5-Cl₂CF₃ 2-CH₃ D-61b *1 5-622 3,5-Cl₂ CF₃ 2-CH₃ D-41a 223.0-224.0 5-6233,5-Cl₂ CF₃ 2-CH₃ (D-47d)Cl 129.0-132.5 5-624 3,5-Cl₂ CF₃ 2-CH₃(D-47d)Br 181.0-183.0 5-625 3,5-Cl₂ CF₃ 2-CH₃ (D-47d)I 180.0-186.0 5-6263,5-Cl₂ CF₃ 2-CH₃ (D-47d)CH₃ 110.0-113.0 5-627 3,5-Cl₂ CF₃ 2-CH₃(D-47d)CF₃ 184.0-186.0 5-628 3,5-Cl₂ CF₃ 2-CH₃ (D-47d)NO₂ 113.0-116.05-629 3,5-Cl₂ CF₃ 2-CH₃ (D-47d)CN *1 5-630 3,5-Cl₂ CF₃ 2-CH₃ (D-47e)Cl*1 5-631 3,5-Cl₂ CF₃ 2-CH₃ (D-47e)Br *1 5-632 3,5-Cl₂ CF₃ 2-CH₃(D-47f)-3,5-Cl₂ 120.0-124.0 5-633 3,5-Cl₂ CF₃ 2-CH₃ (D-48e)Cl *1 5-6343,5-Cl₂ CF₃ 2-CH₃ (D-48e)CN *1 5-635 3,5-Cl₂ CF₃ 2-CH₃ (D-49b)Cl *15-636 3,5-Cl₂ CF₃ 2-CH₃ D-49e 173.0-177.0 5-637 3,5-Cl₂ CF₃ 2-CH₃(D-50b)CH₃ *1 5-638 3,5-Cl₂ CF₃ 2-CH₃ (D-50c)Cl 137.0-141.0 5-6393,5-Cl₂ CF₃ 2-CH₃ (D-50c)Br 178.0-181.0 5-640 3,5-Cl₂ CF₃ 2-CH₃ (D-50c)I*1 5-641 3,5-Cl₂ CF₃ 2-CH₃ (D-51c)Cl 85.0-87.0 5-642 3,5-Cl₂ CF₃ 2-CH₃D-52a 207.0-211.0 5-643 3,5-Cl₂ CF₃ 2-CH₃ D-53a 139.0-144.0 5-6443,5-Cl₂ CF₃ 2-CH₃ (D-53b)Br 251.0-253.0 5-645 3,5-Cl₂ CF₃ 2-CH₃(D-54b)Cl 99.0-102.5 5-646 3,5-Cl₂ CF₂Cl 2-CH₃ CH₂C(O)NHCH₂CF₃171.0-173.0 5-647 3,5-Cl₂-4-CH₃ CF₃ 2-CH₃ CH₂CF₃ *2 5-648 3,5-Cl₂-4-CH₃CF₃ 2-CH₃ CH₂(D-47a) *2 5-649 3,5-Cl₂-4-OH CF₃ 2-CH₃ CH₂(D-47a) *2 5-6503,5-Cl₂-4-OCH₃ CF₃ 2-CH₃ CH₂CF₃ 198.0-199.0 5-651 3,5-Cl₂-4-OCH₃ CF₃2-CH₃ CH₂(D-47a) *2 5-652 3,5-Cl₂-4-OC(O)OBu-t CF₃ 2-CH₃ CH₂(D-47a) *25-653 3,5-Cl₂-4-N(CH₃)₂ CF₃ 2-CH₃ CH₂CF₃ *2 5-654 3,5-Cl₂-4-N(CH₃)₂ CF₃2-CH₃ CH₂(D-47a) *2 5-655 3,5-Cl₂ CF₃ 2-I CH₂OCH₂CF₃ *1 5-656 3,5-Cl₂CF₃ 2-I E-4a *1 5-657 3,5-Cl₂ CF₃ 3-I CH₂C(O)NHCH₂CF₃ *1 5-658 3,5-Cl₂CF₃ 2-CH₃ (E-23b)OCH₃ *1 5-659 3,5-Cl₂ CF₃ 2-CH₃ CH₂C(O)NH(E-4a)86.0-91.0 5-660 3,5-Cl₂ CF₃ 2-CH₃ CH═CH₂ *1 5-661 3,5-Cl₂ CF₃ 2-CH₃CH₂C≡CBr 166.0-169.0 5-662 3,5-Cl₂ CF₃ 2-CH₃ N(CH₃)C(O)NHCH₂CF₃ *1 5-6633,5-Cl₂ CF₃ 2-CH₃ OC(O)NHCH₂CF₃ 111.0-114.0 5-664 3,5-Cl₂ CF₃ 2-CH₃C(O)CH₃ 151.0-154.5 5-665 3,5-Cl₂ CF₃ 2-CH₃ C(O)Et 169.0-172.0 5-6663,5-Cl₂ CF₃ 2-CH₃ D-22a 228.0-230.0 5-667 3,5-Cl₂ CF₃ 2-CH₃ (D-22b)Br *15-668 3,5-Cl₂ CF₃ 2-CH₃ (D-47b)Cl *1 5-669 3,5-Cl₂ CF₂Cl 2-Cl H *1 5-6703-Cl-5-Br CF₃ 2-CH₃ H *1 5-671 3,5-Br₂ CF₃ 2-Cl H 105.0-108.0 5-6723,5-(CF₃)₂ CF₃ 2-CH₃ H *1 5-673 3,5-Cl₂ CF₃ 2-CH₃ D-2a 105.0-110.0 5-6743,5-Cl₂ CF₃ 2-CH₃ (D-50c)CN 118.0-121.0 5-675 3,5-Cl₂ CF₃ 2-CH₃(D-52b)Cl 231.0-234.0 5-676 3,5-Cl₂ CF₃ 2-CH₃ (D-53b)Cl 242.0-243.05-677 3,5-Cl₂ CF₃ 2-Et H *1 5-678 3,5-Cl₂ CF₃ 2-CH₂OCH₃ H 186.0-188.05-679 3,5-Cl₂ CF₃ 2-OCHF₂ H *1 5-680 3,5-Cl₂ CF₃ 2-NO₂ H *1 5-6813,5-Cl₂ CF₃ 2-NH₂ H 190.0-193.0 5-682 3,5-Cl₂ CF₃ 2-NHC(O)CH₃ H *1 5-6833,4,5-Cl₃ CF₃ 2-CH₃ H 153.0-155.0 5-684 3-Cl-5-CF₃ CF₃ 2-CH₃ CH₂CF₃ *15-685 3,5-Cl₂-4-F CF₃ 2-CH₃ CH₂CF₃ *1 5-686 3-Cl-4-F-5-CF₃ CF₃ 2-CH₃CH₂CF₃ *1In Table above, the indications of “5-529 (R)*” and “5-529 (S)*” showoptical isomers in which the absolute configuration of 5-position of4,5-dihydroisoxazole ring is R- and S-configuration, respectively.

TABLE 12

No. (X)_(m) R³ (Y)_(n) R² R¹ m.p. (° C.) 6-001 3,5-Cl₂ CF₃ 2-Cl Et Et *16-002 3,5-Cl₂ CF₃ 2-CH₃ NH₂ CH₃ 138.0-139.0 6-003 3,5-Cl₂ CF₃ 2-CH₃ EtEt *1 6-004 3,5-Cl₂ CF₃ 2-CH₃ NH₂ Et  76.0-78.0 6-005 3,5-Cl₂ CF₃ 2-CH₃NHC(O)CH₃ Et *1 6-006 3,5-Cl₂ CF₃ 2-CH₃ N═C(CH₃)₂ Et *1 6-007 3,5-Cl₂CF₃ 2-CH₃ CH₂CN n-Bu *1 6-008 3,5-Cl₂ CF₃ 2-CH₃ CH₂CN CH₂CN *1 6-0093,5-Cl₂ CF₃ 2-CH₃ OH CH₂Ph 175.0-177.0 6-010 3,5-Cl₂ CF₃ 2-CH₃ OCH₃CH₂Ph *1 6-011 3,5-Cl₂ CF₃ 2-CH₃ OC(O)CH₃ CH₂Ph *1 6-012 3,5-Cl₂ CF₃2-CH₃ OC(O)OCH₃ CH₂Ph *1 6-013 3,5-Cl₂ CF₃ 2-CH₃ OSO₂CH₃ CH₂Ph *1 6-0143,5-Cl₂ CF₃ 2-CH₃ NH₂ CH₂Ph 135.0-136.0 6-015 3,5-Cl₂ CF₃ 2-CH₃ CH₂CNCH₂(D-22a) *1 6-016 3,5-Cl₂ CF₃ 2-CH₃ CH₂C≡CH CH₂(D-22a) *1 6-0173,5-Cl₂ CF₃ 2-CH₃ C(O)CH₃ CH₂(D-22a) *1 6-018 3,5-Cl₂ CF₃ 2-CH₃ C(O)EtCH₂(D-22a) *1 6-019 3,5-Cl₂ CF₃ 2-CH₃ C(O)OCH₃ CH₂(D-22a) *1 6-0203,5-Cl₂ CF₃ 2-CH₃ CH₃ CH₂(D-47a) *1 6-021 3,5-Cl₂ CF₃ 2-CH₃ EtCH₂(D-47a) *1 6-022 3,5-Cl₂ CF₃ 2-CH₃ n-Pr CH₂(D-47a) *1 6-023 3,5-Cl₂CF₃ 2-CH₃ i-Pr CH₂(D-47a) *1 6-024 3,5-Cl₂ CF₃ 2-CH₃ c-Pr CH₂(D-47a) *16-025 3,5-Cl₂ CF₃ 2-CH₃ t-Bu CH₂(D-47a) *1 6-026 3,5-Cl₂ CF₃ 2-CH₃CH₂CF₃ CH₂(D-47a) *1 6-027 3,5-Cl₂ CF₃ 2-CH₃ CH₂OCH₃ CH₂(D-47a) *1 6-0283,5-Cl₂ CF₃ 2-CH₃ CH₂CH₂OCH₃ CH₂(D-47a) *1 6-029 3,5-Cl₂ CF₃ 2-CH₃CH₂SCH₃ CH₂(D-47a) *1 6-030 3,5-Cl₂ CF₃ 2-CH₃ CH₂C(O)OCH₃ CH₂(D-47a) *16-031 3,5-Cl₂ CF₃ 2-CH₃ CH₂CN CH₂(D-47a) *1 6-032 3,5-Cl₂ CF₃ 2-CH₃CH₂CH═CH₂ CH₂(D-47a) *1 6-033 3,5-Cl₂ CF₃ 2-CH₃ CH₂C≡CH CH₂(D-47a) *16-034 3,5-Cl₂ CF₃ 2-CH₃ C(O)CH₃ CH₂(D-47a) *1 6-035 3,5-Cl₂ CF₃ 2-CH₃C(O)Et CH₂(D-47a) *1 6-036 3,5-Cl₂ CF₃ 2-CH₃ C(O)Pr-n CH₂(D-47a) *16-037 3,5-Cl₂ CF₃ 2-CH₃ C(O)Pr-i CH₂(D-47a) *1 6-038 3,5-Cl₂ CF₃ 2-CH₃C(O)Pr-c CH₂(D-47a) *1 6-039 3,5-Cl₂ CF₃ 2-CH₃ C(O)Bu-t CH₂(D-47a) *16-040 3,5-Cl₂ CF₃ 2-CH₃ C(O)CH₂OCH₃ CH₂(D-47a)  53.0-55.0 6-041 3,5-Cl₂CF₃ 2-CH₃ C(O)CH═CH₂ CH₂(D-47a) *1 6-042 3,5-Cl₂ CF₃ 2-CH₃ C(O)PhCH₂(D-47a) *1 6-043 3,5-Cl₂ CF₃ 2-CH₃ C(O)OCH₃ CH₂(D-47a) *1 6-0443,5-Cl₂ CF₃ 2-CH₃ C(O)OEt CH₂(D-47a) *1 6-045 3,5-Cl₂ CF₃ 2-CH₃C(O)OPr-i CH₂(D-47a) *1 6-046 3,5-Cl₂ CF₃ 2-CH₃ C(O)OBu-i CH₂(D-47a) *16-047 3,5-Cl₂ CF₃ 2-CH₃ C(O)OCH₂CH₂Cl CH₂(D-47a) *1 6-048 3,5-Cl₂ CF₃2-CH₃ C(O)OCH₂CH₂OCH₃ CH₂(D-47a) *1 6-049 3,5-Cl₂ CF₃ 2-CH₃C(O)OCH₂CH═CH₂ CH₂(D-47a) *1 6-050 3,5-Cl₂ CF₃ 2-CH₃ C(O)SCH₃ CH₂(D-47a)*1 6-051 3,5-Cl₂ CF₃ 2-CH₃ SO₂CH₃ CH₂(D-47a) *1 6-052 3,5-Cl₂ CF₃ 2-CH₃NH₂ CH₂(D-47a) 126.0-130.0 6-053 3,5-Cl₂ CF₃ 2-CH₃ N(CH₃)₂ CH₂(D-47a) *16-054 3,5-Cl₂ CF₃ 2-CH₃ Et CH₂(D-48e)Cl *1 6-055 3,5-Cl₂ CF₃ 2-CH₃ c-PrCH₂(D-49a) *1 6-056 3,5-Cl₂ CF₃ 2-CH₃ C(O)Et CH₂(D-50a) *1 6-057 3,5-Cl₂CF₃ 2-CH₃ —CH₂CH₂SCH₂CH₂— 209.5-211.5 6-058 3,5-Cl₂ CF₃ 2-CH₃ CH₃N(CH₃)Ph 153.0-154.0 6-059 3,5-Cl₂ CF₃ 2-CH₃ Et N(CH₃₎Ph  78.0-79.06-060 3,5-Cl₂ CF₃ 2-CH₃ CH₂OCH₃ N(CH₃)Ph  72.0-73.0 6-061 3,5-Cl₂ CF₃2-CH₃ CH₂CH ═ CH₂ N(CH₃)Ph  76.0-77.0 6-062 3,5-Cl₂ CF₃ 2-CH₃ CH₂C≡CHN(CH₃)Ph  83.0-84.0 6-063 3,5-Cl₂ CF₃ 2-CH₃ CH₂CN N(CH₃)Ph  69.0-70.06-064 3,5-Cl₂ CF₃ 2-CH₃ C(O)CH₃ N(CH₃)Ph  82.0-83.0 6-065 3,5-Cl₂ CF₃2-CH₃ C(O)OCH₃ N(CH₃)Ph  70.0-71.0 6-066 3,5-Cl₂ CF₃ 2-CH₃ CH₃ NH(D-50a)107.0-109.0 6-067 3,5-Cl₂ CF₃ 2-CH₃ Et NH(D-50a) 185.0-187.0 6-0683,5-Cl₂ CF₃ 2-CH₂— H 234.0-236.0 6-069 3,5-Cl₂ CF₃ 2-CH₂— CH₃ *1 6-0703,5-Cl₂ CF₃ 2-CH₂— CH₂(D-47a) *1 6-071 3,5-Cl₂ CF₃ 2-N(CH₃)CH₂—CH₂(D-47a) *1 6-072 3,5-Cl₂ CF₃ 2-N═CH— H 249.0-251.0 6-073 3,5-Cl₂ CF₃2-N═CH— CH₂(D-47a) *1 6-074 3,5-Cl₂ CF₂Cl 2-CH₃ C(O)CH₃ CH₂CF₃ *1 6-0753,5-Br₂ CF₃ 2-CH₃ C(O)CH₃ CH₂CF₃ *1 6-076 3,5-Br₂ CF₃ 2-CH₃ C(O)CH₃CH₂(D-47a) *1 6-077 3,5-Cl₂ CF₃ 2-CH₃ C(O)OCH₃ CH₂CF₃ *2 6-078 3,5-Cl₂CF₃ 2-CH₃ CH₂OCH₃ CH₂(D-22a) *1 6-079 3,5-Cl₂ CF₃ 2-CH₃ CH₂OEtCH₂(D-47a) *1 6-080 3,5-Cl₂ CF₃ 2-CH₃ C(O)OCH₃ CH(CH₃)(D-47a) *26-080(+)* 98% e.e. [α]_(D) ^(22.4) +35.40° (CHCl₃, c = 0.397) *26-080(−)* 99% e.e. [α]_(D) ^(22.2) −37.20° (CHCl₃, c = 0.473) *2 6-0813,5-Cl₂ CF₃ 2-CH₃ C(O)CH₃ N(CH₃)(D-47a) *1 6-082 3,5-Cl₂ CF₃ 2-CH₃C(O)OCH₃ N(CH₃)(D-47a) *1 6-083 3,5-Cl₂ CF₃ 2-CH₃ C(O)CH₃ N(CH₃)(D-50a)*2 6-084 3,5-Cl₂ CF₃ 2-CH₃ C(O)OCH₃ N(CH₃)(D-50a) *1 6-085 3,5-Cl₂ CF₃2-CH₃ —C(O)CH₂CH₂CH₂— *1 6-086 3,5-Cl₂ CF₃ 2-CH₃ —C(O)CH₂CH₂C(O)— *16-087 3,5-Cl₂ CF₃ 2-CH₃ —CH₂CH₂N(Ph)CH₂CH₂—  84.0-88.0 6-088 3,5-Cl₂ CF₃2-CH₃ —CH₂CH₂N(D-47a)CH₂CH₂—  87.0-92.0 6-089 3,5-Cl₂ CF₃ 2-CH₃ C(O)EtCH₃ *1 6-090 3,5-Cl₂ CF₃ 2-CH₃ C(O)CF₃ CH₃ 181.0-183.0 6-091 3,5-Cl₂ CF₃2-CH₃ C(O)OCH₂CH₂CF₃ CH₃ 148.0-150.0 6-092 3,5-Cl₂ CF₃ 2-CH₃ CH₂OEtCH₂OEt *1 6-093 3,5-Cl₂ CF₃ 2-CH₃ C(O)CH₃ CH₂OEt *1 6-094 3,5-Cl₂ CF₃2-CH₃ CH₃ CH₂OCH₂CF₃ *1 6-095 3,5-Cl₂ CF₃ 2-CH₃ C(O)CH₃ CH₂OCH₂CF₃ *16-096 3,5-Cl₂ CF₃ 2-CH₃ C(O)OCH₃ CH₂CH₂OCH₃ *1 6-097 3,5-Cl₂ CF₃ 2-CH₃CH₃ CH₂(E-10a) *1 6-098 3,5-Cl₂ CF₃ 2-CH₃ C(O)CH₃ CH₂(E-10a) *1 6-0993,5-Cl₂ CF₃ 2-CH₃ C(O)OCH₃ CH₂(E-10a) *1 6-100 3,5-Cl₂ CF₃ 2-CH₃ C(O)CH₃E-4a *1 6-101 3,5-Cl₂ CF₃ 2-CH₃ CH₃ CH₂CH═NOCH₃ *1 6-102 3,5-Cl₂ CF₃2-CH₃ C(O)CH₃ CH₂CH═NOCH₃ *1 6-103 3,5-Cl₂ CF₃ 2-CH₃ C(O)OCH₃CH₂CH═NOCH₃ *1 6-104 3,5-Cl₂ CF₃ 2-CH₃ C(O)OCH₃ CH₂C(O)NHCH₂CF₃115.0-120.0 6-105 3,5-Cl₂ CF₃ 2-CH₃ C(O)OCH₃ CH₂(Ph—4-OCH₃) *1 6-1063,5-Cl₂ CF₃ 2-CH₃ C(O)OCH₃ CH₂(Ph—4-NO₂) *1 6-107 3,5-Cl₂ CF₃ 2-CH₃C(O)OCH₃ CH₂(Ph—4-Ph) *1 6-108 3,5-Cl₂ CF₃ 2-CH₃ C(O)OBu-t CH₂(D-14b)CF₃*1 6-109 3,5-Cl₂ CF₃ 2-CH₃ C(O)OCH₃ CH₂(D-61b) *1 6-110 3,5-Cl₂ CF₃2-CH₃ C(O)OCH₃ CH₂(D-47a) · Q1  70.0-100.0 6-111 3,5-Cl₂ CF₃ 2-CH₃Ph—4-F CH₂(D-47a) *1 6-112 3,5-Cl₂ CF₃ 2-CH₃ C(O)OCH₃ CH₂(D-50a) *16-113 3,5-Cl₂ CF₃ 2-CH₃ —CH₂CH₂CH₂CH[C(O)NHCH₂CF₃]— *1 6-114 3,5-Cl₂ CF₃2-CH₃ —CH₂OCH₂CH₂— *1 6-115 3,5-Cl₂ CF₃ 2-CH₃ —CH₂SCH₂CH₂— *1 6-1163,5-Cl₂ CF₃ 2-CH₃ —CH₂SO₂CH₂CH₂— 206.0-208.0 6-117 3,5-Cl₂ CF₃ 2-CH₃—CH₂CH₂OCH₂CH₂— 217.0-219.0 6-118 3,5-Cl₂ CF₃ 2-CH₃ —CH₂CH₂SO₂CH₂CH₂—223.0-226.0 6-119 3,5-Cl₂ CF₃ 2-CH₃ —CH₂CH₂N(CH₃)CH₂CH₂— *1 6-1203,5-Cl₂ CF₃ 2-CH₃ C(O)OCH₃ OCH₃ *1 6-121 3,5-Cl₂ CF₃ 2-CH₃ C(O)OCH₃N(CH₃)₂ *1 6-122 3,5-Cl₂ CF₃ 2-CH₃ C(O)CH₃ C(O)CH₃ *1 6-123 3,5-Cl₂ CF₃2-CH₃ —CH₂CH(CH₂F)OC(O)— *1 6-124 3,5-Cl₂ CF₃ 2-CH₃ C(O)OCH₃ C(O)N(CH₃)₂*1 6-125 3,5-Cl₂ CF₃ 2-CH₃ CH₃ C(O)NHEt *1 6-126 3,5-Cl₂ CF₃ 2-CH₃ CH₃C(O)NHCH₂CF₃ *1 6-127 3,5-Cl₂ CF₃ 2-CH₃ —CH₂CH₂N(CH₂CF₃)C(O)—167.0-170.0 6-128 3,5-Cl₂ CF₃ 2-C(═CH₂)— CH₂CF₃ 141.0-144.0 6-1293,5-Cl₂ CF₃ 2-CH₃ CH₃ E-4a 155.0-157.0 6-130 3,5-Cl₂ CF₃ 2-CH₃ CH₂OCH₃E-4a *1 6-131 3,5-Cl₂ CF₃ 2-CH₃ C(O)Et E-4a *1 6-132 3,5-Cl₂ CF₃ 2-CH₃C(O)Pr-i E-4a *1 6-133 3,5-Cl₂ CF₃ 2-CH₃ CH₃ E-6a 146.0-151.0 6-1343,5-Cl₂ CF₃ 2-CH₃ CH₃ CH₃ 166.5-168.5In Table above, the indications of “6-080 (+)*” and “6-080 (−)*” showoptically active forms of 1-(2-pyridyl)ethylamine moiety.

TABLE 13

No. (X)_(m) R³ (Y)_(n) R² R¹ m.p. (°C.) 7-001 3,5-Cl₂ CF₃ — H H227.0-232.0 7-002 3,5-Cl₂ CF₃ — H CH₂CF₃ *1 7-003 3,5-Cl₂ CF₃ — HCH₂(D-22a) *1 7-004 3,5-Cl₂ CF₃ — H CH₂(D-47a) 165.0-167.0 7-005 3,5-Cl₂CF₃ 2-F H CH₂(D-22a) 171.0-173.0 7-006 3,5-Cl₂ CF₃ 2-Cl H CH₂(D-22a) 90.0-92.0 7-007 3,5-Cl₂ CF₃ 2-CH₃ H CH₂CF₃ *1 7-008 3,5-Cl₂ CF₃ 2-CH₃ HCH₂(D-22a) *1 7-009 3,5-Cl₂ CF₃ 2-CH₃ H CH₂(D-47a) *1 7-010 3,5-Cl₂ CF₃2-CH₃ H N(CH₃)Ph 100.0-111.0

TABLE 14

No. (X)_(m) R³ (Y)_(n) R^(1a) R^(2a) m.p. (°C.) 8-001 3,5-Cl₂ CF₃ ——N(CH₃)CH═CHS— *1 8-002 3,5-Cl₂ CF₃ 2-CH₃ —N(CH₃)CH═CHS— *1 8-0033,5-Cl₂ CF₃ 2-CH₃ —N(Pr-n)CH═CHS— *1 8-004 3,5-Cl₂ CF₃ 2-CH₃—N(CH₃)N═CHCH₂S— *1 8-005 3,5-Cl₂ CF₃ 2-CH₃ O —N(CH₃)CH═CHCH═N— *1 8-0063,5-Cl₂ CF₃ 2-CH₃ O —N(CH₃)N═CHS— *1 8-007 3,5-Cl₂ CF₃ 2-CH₃ O—N(CH₃)N═CClCH═CH— *2

TABLE 15

Substituent G in the above-mentioned formula is the structure of G-3,G-6, G-18 or G-20 mentioned below. No. G (X)_(m) R³ (Y)_(n) R² R¹ m.p.(° C.) 9-001 G-3 6-F CF₃ — H CH₂CF₃ 175.0-177.0 9-002 G-3 6-Cl CF₃ — HCH₂CF₃ 192.0-195.0 9-003 G-3 5-Br CF₃ 2-CH₃ H CH₂CF₃ *1 9-004 G-3 6-OCH₃CF₃ — H CH₂CF₃ 150.0-152.0 9-005 G-6 4,6-Cl₂ CF₃ — H CH₂CF₃ 140.0-142.09-006 G-6 4,6-Cl₂ CF₃ 2-CH₃ H CH₂CF₃ 131.0-134.0 9-007 G-18 — CF₃ — HCH₂CF₃ 156.0-157.0 9-008 G-20 4-CF₃ CF₃ 2-CH₃ H CH₂CF₃ *1 9-009 G-204-CF₃ CF₃ 2-CH₃ H CH₂(D-47a) *1 9-010 G-13 5-Cl CF₃ 2-CH₃ H CH₂CF₃ *19-011 G-13 5-Cl CF₃ 2-CH₃ H CH₂(D-47a) *1

TABLE 16

No. (X)_(m) A¹ A² A³ (Y)_(n) R¹ m.p. (° C.) 10-001 3,5-Cl₂ N C C —CH₂CF₃ *1 10-002 3,5-Cl₂ N C C — CH₂(D-47a) *1 10-003 3,5-Cl₂ N(O) C C —CH₂CF₃ *1 10-004 3,5-Cl₂ C N C — CH₂CF₃ *1 10-005 3,5-Cl₂ C N C —CH₂(D-47a) *1

TABLE 17

No. (X)_(m) R³ (Y)_(n) R m.p. (° C.) 11-001 3-Cl CF₃ — C(O)OH220.0-225.0 11-002 3-Cl CF₃ — C(O)OCH₃ 100.0-101.0 11-003 4-Cl CF₃ —C(O)OH 255.0-257.0 11-004 4-Cl CF₃ — C(O)OCH₃ *1 11-005 3-I CF₃ 2-CH₃C(O)OH 169.0-172.0 11-006 3-I CF₃ 2-CH₃ C(O)OCH₃ *1 11-007 3-NO₂ CF₃2-CH₃ C(O)OCH₃ *1 11-008 3,4-F₂ CF₃ — C(O)OH 246.0-248.0 11-009 3,4-F₂CF₃ — C(O)OCH₃ 132.0-133.0 11-010 2,4-Cl₂ CF₃ — C(O)OH 104.0-106.011-011 2,4-Cl₂ CF₃ — C(O)OCH₃ 103.0-106.0 11-012 2,5-Cl₂ CF₃ — C(O)OH 97.0-100.0 11-013 2,5-Cl₂ CF₃ — C(O)OCH₃ 163.0-165.0 11-014 3,4-Cl₂ H —C(O)OCH₃ 115.0-117.0 11-015 3,4-Cl₂ CH₃ — C(O)OCH₃  98.0-100.0 11-0163,4-Cl₂ CF₃ — C(O)OH 215.0-217.0 11-017 3,4-Cl₂ CF₃ — C(O)OCH₃ 95.0-97.0 11-018 3,4-Cl₂ CF₃ — C(O)OBu-t  94.0-95.0 11-019 3,4-Cl₂ CF₃— C(O)OCH₂Ph  94.0-95.0 11-020 3,4-Cl₂ Ph — C(O)OCH₃ 143.0-145.0 11-0213,5-Cl₂ CF₃ — CH₂OH 108.0-110.0 11-022 3,5-Cl₂ CF₃ — OH 153.0-155.511-023 3,5-Cl₂ CF₃ — OCH₃  93.0-96.5 11-024 3,5-Cl₂ CF₃ — NO₂161.0-162.0 11-025 3,5-Cl₂ CF₃ — NH₂  98.0-99.0 11-026 3,5-Cl₂ CF₃ — CN140.0-142.0 11-027 3,5-Cl₂ CF₃ — C(O)OH 237.0-240.0 11-028 3,5-Cl₂ CF₃ —C(O)OCH₃  94.0-96.0 11-029 3,5-Cl₂ CF₃ 2-F CH₂Br *2 11-030 3,5-Cl₂ CF₃2-F CH₂OC(O)CH₃ *2 11-031 3,5-Cl₂ CF₃ 2-F CH₂OH *1 11-032 3,5-Cl₂ CF₃2-F C(O)OH 172.0-174.0 11-033 3,5-Cl₂ CF₃ 3-F Br 136.0-138.0 11-0343,5-Cl₂ CF₃ 3-F C(O)OH *1 11-035 3,5-Cl₂ CF₃ 3-F C(O)OEt  94.0-96.011-036 3,5-Cl₂ CF₃ 2-Cl OSO₂CF₃ 154.0-157.5 11-037 3,5-Cl₂ CF₃ 2-ClC(O)OH 150.0-151.0 11-038 3,5-Cl₂ CF₃ 2-Cl C(O)OCH₃ *2 11-039 3,5-Cl₂CF₃ 3-Cl Br *2 11-040 3,5-Cl₂ CF₃ 3-Cl C(O)OH 187.0-188.0 11-041 3,5-Cl₂CF₃ 3-Cl C(O)OEt *1 11-042 3,5-Cl₂ CF₃ 2-Br C(O)OCH₃  83.0-86.0 11-0433,5-Cl₂ CF₃ 2-I CH₃ 130.0-132.0 11-044 3,5-Cl₂ CF₃ 2-I CH₂Br *1 11-0453,5-Cl₂ CF₃ 2-I CH₂OC(O)CH₃ *1 11-046 3,5-Cl₂ CF₃ 2-I CH₂OH *1 11-0473,5-Cl₂ CF₃ 2-I C(O)OH *1 11-048 3,5-Cl₂ CF₃ 2-I C(O)OCH₃ *2 11-0493,5-Cl₂ CF₃ 2-CH₃ NO₂ 135.0-136.0 11-050 3,5-Cl₂ CF₃ 2-CH₃ NH₂ *1 11-0513,5-Cl₂ CF₃ 2-CH₃ F  67.0-68.0 11-052 3,5-Cl₂ CF₃ 2-CH₃ Br 113.0-114.511-053 3,5-Cl₂ CF₃ 2-CH₃ C(O)OH 150.0-152.0 11-054 3,5-Cl₂ CF₃ 2-CH₃C(O)OCH₃  96.0-99.5 11-055 3,5-Cl₂ CF₃ 2-CH₃ C(O)OEt n_(D) ^(21.4°)^(C.)1.5474 11-056 3,5-Cl₂ CF₃ 2-CH₃ C(O)OCH₂ *2 (D-47a) 11-057 3,5-Cl₂CF₃ 2-CH₃ C(O)(D-14a) *1 11-058 3,5-Cl₂ CF₃ 2-CH₃ C(O)(D-38a)  58.0-59.011-059 3,5-Cl₂ CF₃ 2-Et C(O)OCH₃ *2 11-060 3,5-Cl₂ CF₃ 2-CH₂Br C(O)OCH₃*2 11-061 3,5-Cl₂ CF₃ 2-CF₃ F *1 11-062 3,5-Cl₂ CF₃ 2-CF₃ CN *1 11-0633,5-Cl₂ CF₃ 2-CF₃ C(O)OCH₃ *2 11-064 3,5-Cl₂ CF₃ 2-OH NO₂ 110.0-113.011-065 3,5-Cl₂ CF₃ 2-OH NH₂ 178.0-181.0 11-066 3,5-Cl₂ CF₃ 2-OCH₃OSO₂CF₃ *1 11-067 3,5-Cl₂ CF₃ 2-OCH₃ C(O)OH *1 11-068 3,5-Cl₂ CF₃ 2-OCH₃C(O)OEt 142.0-144.0 11-069 3,5-Cl₂ CF₃ 2-OCF₃ NH₂  81.5-84.0 11-0703,5-Cl₂ CF₃ 2-OCF₃ I *1 11-071 3,5-Cl₂ CF₃ 2-OCF₃ C(O)OCH₃ *1 11-0723,5-Cl₂ CF₃ 2-SCH₃ C(O)OH 151.0-152.0 11-073 3,5-Cl₂ CF₃ 2-SCH₃ C(O)OCH₃*2 11-074 3,5-Cl₂ CF₃ 2-NO₂ Br 179.0-181.0 11-075 3,5-Cl₂ CF₃ 2-NO₂C(O)OEt 160.0-162.0 11-076 3,5-Cl₂ CF₃ 2-NH₂ Br *2 11-077 3,5-Cl₂ CF₃2-NH₂ C(O)OH *2 11-078 3,5-Cl₂ CF₃ 2-NH₂ C(O)OEt *2 11-079 3,5-Cl₂ CF₃2-Ph C(O)OH *1 11-080 3,5-Cl₂ CF₃ 2-Ph C(O)OCH₃ *1 11-081 3,5-Cl₂ CF₃2,3-F₂ CH₃ *1 11-082 3,5-Cl₂ CF₃ 2,3-F₂ CH₂Br *1 11-083 3,5-Cl₂ CF₃2,3-F₂ CH₂OH *1 11-084 3,5-Cl₂ CF₃ 2,6-Cl₂ C(O)OEt *2 11-085 3,5-Cl₂ CF₃2-Cl—6-CH₃ NH₂ *1 11-086 3,5-Cl₂ CF₃ 2,6-(CH₃)₂ OH 209.0-214.0 11-0873,5-Cl₂ CF₃ 2,6-(CH₃)₂ OSO₂CF₃ n_(D) ^(21.6°C.)l.5194 11-088 3,5-Cl₂ CF₃2,6-(CH₃)₂ C(O)OH 128.5-130.5 11-089 3,5-Cl₂ CF₃ 2,6-(CH₃)₂ C(O)OCH₃135.0-138.0 11-090 3,5-Cl₂ CF₂Cl 2-Cl C(O)OH 100.0-104.5 11-091 3,5-Cl₂CF₂Cl 2-CH₃ C(O)OH  76.0-80.0 11-092 3,5-Cl₂ CF₂Cl 2-CH₃ C(O)OEt *111-093 3,5-Br₂ CF₃ 2-Cl C(O)OH 144.5-147.0 11-094 3,5-Br₂ CF₃ 2-CH₃C(O)OH 135.0-138.5 11-095 3,5-Br₂ CF₃ 2-CH₃ C(O)OEt *1 11-096 3- CF₃ —C(O)OH 208.0-210.0 OCH₂O-4 11-097 3- CF₃ — C(O)OCH₃ 172.0-173.0 OCH₂O-411-098 3,5-Cl₂ CF₃ — Br 122.0-124.0 11-099 3,5-Cl₂ CF₃ — I 144.0-146.011-100 3,5-Cl₂ CF₃ — CH₂Cl  98.0-100.0 11-101 3,5-Cl₂ CF₃ 2-F CH₃ 87.0-89.0 11-102 3,5-Cl₂ CF₃ 2-F CHBr₂ *1 11-103 3,5-Cl₂ CF₃ 2-Cl CH₃ 97.0-99.0 11-104 3,5-Cl₂ CF₃ 2-Cl CH₂Br  94.0-97.0 11-105 3,5-Cl₂ CF₃2-Cl CHBr₂ *1 11-106 3,5-Cl₂ CF₃ 2-Cl CH₂OH  32.0-35.0 11-107 3,5-Cl₂CF₃ 2-Cl CH₂OC(O)CH₃ *1 11-108 3,5-Cl₂ CF₃ 2-Cl NO₂  97.0-103.0 11-1093,5-Cl₂ CF₃ 2-Cl NH₂ 158.0-160.0 11-110 3,5-Cl₂ CF₃ 2-Cl CHO 129.0-130.011-111 3,5-Cl₂ CF₃ 2-Br CH₃ 119.0-121.0 11-112 3,5-Cl₂ CF₃ 2-Br CHBr₂ *111-113 3,5-Cl₂ CF₃ 2-Br CH₂OH *1 11-114 3,5-Cl₂ CF₃ 2-Br CH₂OC(O)CH₃ *111-115 3,5-Cl₂ CF₃ 2-I CHBr₂ 125.0-128.0 11-116 3,5-Cl₂ CF₃ 2-I CHO *111-117 3,5-Cl₂ CF₃ 2-CH₃ Cl 115.5-117.0 11-118 3,5-Cl₂ CF₃ 2-CH₃ CH₂Cl*1 11-119 3,5-Cl₂ CF₃ 2-CH₃ CH₂OH *1 11-120 3,5-Cl₂ CF₃ 2-CH₃ CN141.0-142.0 11-121 3,5-Cl₂ CF₃ 2-CH₃ C(O)Cl 140.5-143.0 11-122 3,5-Cl₂CF₃ 3-OH C(O)OEt *1 11-123 3,5-Cl₂ CF₃ 2-NO₂ F  86.0-89.0 11-124 3,5-CF₃ — NO₂ 170.0-172.0 (CF₃)₂ 11-125 3,5-Cl₂ CF₃ 2-OCHF₂ NO₂ *1 11-1263,5-Cl₂ CF₃ 2-OCHF₂ NH₂ *1 11-127 3,5-Cl₂ CF₃ 2-OCHF₂ I *1 11-1283,5-Cl₂ CF₃ 2-NO₂ CH₃ 119.0-122.0 11-129 3-Cl—5-Br CF₃ 2-CH₃ C(O)OEt *111-130 3,5- CF₃ 2-CH₃ C(O)OEt *2 (CF₃)₂ 11-131 3,5-Cl₂ CF₃ 2-OH CH₃145.0-147.0 11-132 3,5-Cl₂ CF₃ 2-OCH₃ CH₃  86.0-89.0

TABLE 18

No. (X)_(m) R³ A¹ A² (Y)_(n) R m.p. (° C.) 12-001 3,5-Cl₂ CF₃ N C — Cl139.0-140.0 12-002 3,5-Cl₂ CF₃ N C — Br 147.0-148.0 12-003 3,5-Cl₂ CF₃ NC — C(O)OH 118.0-120.0 12-004 3,5-Cl₂ CF₃ N C — C(O)OEt 154.0-155.012-005 3,5-Cl₂ CF₃ C N — C(O)OH 195.5-198.5 12-006 3,5-Cl₂ CF₃ C N —C(O)OCH₃ 147.0-151.5

TABLE 19

No. A¹ (Y)_(n) R² R¹ J m.p. (° C.) 13-001 C — H CH₂CF₃ H 153.0-154.013-002 C — H CH₂CF₃ Cl 158.0-160.0 13-003 C — H CH₂Ph H 191.0-192.013-004 C — H CH₂Ph Cl 131.0-133.0 13-005 C — H CH₂(D-47a) H 166.0-168.013-006 C 2-CH₃ H CH₂CF₃ H 190.5-194.0 13-007 C 2-CH₃ H CH₂CF₃ Cl134.0-137.0 13-008 C 2-CH₃ H CH₂(D-47a) H 163.0-164.0 13-009 C 2-CH₃ HCH₂(D-47a) Cl 174.0-176.0 13-010 C 3-CH₃ H CH₂CF₃ H 163.0-168.0

TABLE 20

No. X¹ (X²)_(m1) R³ m.p./b.p.(° C.) 14-001 Cl 5-Cl Pr-i n_(D)^(20.6°C.)1.5472 14-002 Cl 5-Cl CHF₂ n_(D) ^(20.6°C.)l.5370 14-003 Cl5-Cl CF₃ 64.0-66.0/2 mmHg 14-004 Cl 5-Cl CF₂Cl *2 14-005 Cl 5-Cl CF₂CF₃*2 14-006 Cl 5-Cl CH₂OCH₂CF₃ *2 14-007 Cl 5-Cl CH₂Si(CH₃)₃ *2 14-008 Cl5-Cl D-47a *2 14-009 Cl 5-Br CF₃ *2 14-010 Cl 5-CH₃ CF₃ *2 14-011 Cl5-CH₃—6-F CF₃ n_(D) ^(20.6°C.)1.4895 14-012 Cl 4-F—5-Cl CF₃ *2 14-013 Cl4,5-Cl₂ CF₃ *1 14-014 Cl 4-NHC(O)OBu-t—5-Cl CF₃ 67.0-68.0 14-015 Br —CF₃ n_(D) ^(20.7°C.)1.5258 14-016 Br 5-Br CF₃ *2 14-017 CF₃ — CF₃ n_(D)^(20.6°C.)l.4228 14-018 CF₃ 5-Cl CF₃ *2 14-019 CF₃ 5-NO₂ CF₃ n_(D)^(20.6°C.)l.4553 14-020 CF₃ 4-F—5-Cl CF₃ *2 14-021 T-4 — CF₃ *2 14-022OCF₂CHFOCF₂CF₂CF₃ — CF₃ *2 14-023 OCH₂Ph — CF₃ *2 14-024 OCH₂(Ph—2-Cl) —CF₃ *2 14-025 O[(D-47f)—3-Cl—5-CF₃] — CF₃ *2 14-026 SCF₃ — CF₃ *2 14-027NO₂ — CF₃ *2Among the compounds of the present invention, ¹H NMR data of thecompounds that the measured value of molecular ion peak, melting pointor refractive index is not shown are shown in Table 21.In the meantime, the indication of “(A)” in the table shows a conditionin which tetramethylsilane is used as standard substance in chloroform-dsolvent and measurement is carried out at 300 MHz (CDCl₃, Me₄Si, 300MHz), hereinafter, the indication “(B)” shows the measurement conditionof (CDCl₃, Me₄Si, 400 MHz), the indication of “(C)” shows themeasurement condition of (CDCl₃-DMSO-d₆, Me₄Si, 300 MHz), and theindication of “(D)” shows the measurement condition of (CDCl₃-DMSO-d₆,Me₄Si, 400 MHz).

TABLE 21 No. ¹H NMR 3-010 (A) δ 8.55-8.6 (m, 1H), 7.15-8.05 (m, 15H),6.95-7.1 (m, 1H), 5.20 (s, 2H), 4.76 (d, J = 4.4 Hz, 2H), 4.10 (d, J =17.2 Hz, 1H), 3.78 (d, J = 17.2 Hz, 1H). 3-034 (A) δ 7.2-7.5 (m, 7H),4.55-4.7 (m, 2H), 4.06 (d, J = 17.1 Hz, 1H), 3.67 (d, J = 17.1 Hz, 1H),2.38 (s, 3H). 3-059 (B) δ 7.9-7.95 (m, 2H), 7.8-7.9 (m, 1H), 7.7-7.8 (m,2H), 7.51 (s, 2H), 7.4-7.45 (m, 1H), 5.02 (d, J = 7.0 Hz, 2H), 4.12 (d,J = 17.0 Hz, 1H), 3.73 (d, J = 17.0 Hz, 1H). 3-064 (A) δ 7.84 (d, J =8.4 Hz, 2H), 7.74 (d, J = 8.4 Hz, 2H), 7.51 (bs, 2H), 7.43 (bs, 1H),6.42 (bs, 1H), 4.63 (t, J = 5.1 Hz, 1H), 4.11 (d, J = 17.4 Hz, 1H),3.65-3.85 (m, 3H), 3.5-3.65 (m, 4H), 1.24 (t, J = 6.8 Hz, 6H). 3-067 (A)δ 7.6-7.8 (m, 3H), 7.54 (d, J = 7.8 Hz, 2H), 7.44 (bs, 2H), 7.38 (bs,1H), 3.4-4.25 (m, 7H), 4.04 (d, J = 17.7 Hz, 1H), 3.69 (d, J = 17.4 Hz,1H). 3-069 (A) δ 7.82 (d, J = 8.7 Hz, 2H), 7.71 (d, J = 8.7 Hz, 2H),7.51 (bs, 2H), 7.42 (bs, 1H), 6.71 (bs, 1H), 4.11 (d, J = 17.4 Hz, 1H),3.6-3.95 (m, 4H), 3.74 (d, J = 17.1 Hz, 1H), 3.48 (t, J = 6.3 Hz, 2H),2.55-2.7 (m, 1H), 2.0-2.15 (m, 1H), 1.6-1.75 (m, 1H). 3-072 (A) δ 7.85(d, J = 8.4 Hz, 2H), 7.73 (d, J = 8.4 Hz, 2H), 7.51 (bs, 2H), 7.4-7.5(m, 1H), 6.44 (bs, 1H), 4.75 (t, J = 4.8 Hz, 1H), 4.1-4.2 (m, 2H), 4.10(d, J = 17.4 Hz, 1H), 3.75-3.9 and 3.6-3.65 (m, 2H), 3.72 (d, J = 17.4Hz, 1H), 3.6-3.65 (m, 2H), 2.0-2.15 (m, 1H), 1.35-1.45 (m, 1H). 3-074(A) δ 7.82 (d, J = 8.4 Hz, 2H), 7.72 (d, J = 8.4 Hz, 2H), 7.51 (bs, 2H),7.4-7.45 (m, 1H), 6.53 (bs, 1H), 4.09 (d, J = 17.4 Hz, 1H), 3.72 (s,2H), 3.71 (d, J = 17.4 Hz, 1H), 2.92 (s, 3H), 1.72 (s, 6H). 3-077 (A) δ9.79 (s, 1H), 7.89 (d, J = 8.4 Hz, 2H), 7.76 (d, J = 8.4 Hz, 2H), 7.61(bs, 2H), 7.51 (bs, 1H), 6.91 (bs, 1H), 4.46 (d, J = 4.5 Hz, 2H), 4.11(d, J = 17.4 Hz, 1H), 3.72 (d, J = 17.1 Hz, 1H). 3-078 (A) δ 9.27 (bs,1H), 7.85 (d, J = 8.5 Hz, 2H), 7.74 (d, J = 8.7 Hz, 2H), 7.60 and 6.93(t, J = 4.4 Hz, 1H), 7.51 (bs, 2H), 7.44 (bs, 1H), 6.71 (bs, 1H), 4.37and 4.26 (d, J = 4.7 Hz, 2H), 4.11 (d, J = 16.8 Hz, 1H), 3.72 (d, J =17.4 Hz, 1H). 3-079 (A) δ 7.8-7.9 (m, 2H), 7.7-7.8 (m, 2H), 7.45-7.55(m, 2H), 7.45-7.55 and 6.82 (t, J = 4.4 Hz, 1H), 7.43 (t, J = 2.0 Hz,1H), 6.71 and 6.60 (bs, 1H), 4.31 and 4.24 (t, J = 4.5 Hz, 2H), 4.11 (d,J = 17.4 Hz, 1H), 3.94 and 3.88 (s, 3H), 3.72 (d, J = 17.4 Hz, 1H).3-082 (A) δ 7.90 (d, J = 8.7 Hz, 2H), 7.73 (d, J = 8.7 Hz, 2H), 7.52 (s,2H), 7.43 (s, 1H), 7.10 (t, J = 4.8 Hz, 1H), 4.21 (d, J = 4.8 Hz, 2H),4.12 (d, J = 17.4 Hz, 1H), 3.74 (d, J = 17.4 Hz, 1H). 3-083 (A) δ 7.87(d, J = 8.1 Hz, 2H), 7.74 (d, J = 8.1 Hz, 2H), 7.52 (s, 2H), 7.43 (s,1H), 6.73 (bs, 1H), 4.26 (d, J = 5.1 Hz, 2H), 4.11 (d, J = 17.4 Hz, 1H),3.82 (s, 3H), 3.73 (d, J = 17.4 Hz, 1H). 3-087 (A) δ 8.52 (bs, 1H), 7.97(bs, 1H), 7.88 (d, J = 8.4 Hz, 2H), 7.7-7.8 (m, 3H), 7.51 (s, 2H), 7.43(s, 1H), 4.45 (d, J = 4.8 Hz, 2H), 4.11 (d, J = 17.4 Hz, 1H), 3.74 (d, J= 17.4 Hz, 1H). 3-089 (A) δ 7.84 (d, J = 8.5 Hz, 2H), 7.73 (d, J = 8.5Hz, 2H), 7.51 (bs, 2H), 7.43 (bs, 1H), 6.18 (bs, 1H), 5.85-6.05 (m, 1H),5.2-5.35 (m, 2H), 4.05-4.15 (m, 3H), 3.72 (d, J = 17.4 Hz, 1H). 3-107(A) δ 7.82 (d, J = 8.1 Hz, 2H), 7.72 (d, J = 8.4 Hz, 2H), 7.55 (s, 1H),7.51 (bs, 2H), 7.43 (bs, 1H), 6.27 (bs, 1H), 4.48 (d, J = 5.1 Hz, 2H),4.10 (d, J = 17.1 Hz, 1H), 3.79 (s, 3H), 3.71 (d, J = 17.4 Hz, 1H).3-108 (A) δ 7.82 (d, J = 8.1 Hz, 2H), 7.72 (d, J = 8.4 Hz, 2H), 7.51(bs, 2H), 7.4-7.45 (m, 1H), 6.34 (bs, 1H), 4.48 (d, J = 5.4 Hz, 2H),4.10 (d, J = 17.1 Hz, 1H), 3.81 (s, 3H), 3.71 (d, J = 17.4 Hz, 1H).3-110 (A) δ 7.82 (d, J = 8.1 Hz, 2H), 7.74 (d, J = 8.7 Hz, 2H), 7.51(bs, 2H), 7.43 (bs, 1H), 6.36 (bs, 1H), 6.17 (s, 1H), 4.65 (d, J = 5.7Hz, 2H), 4.08 (d, J = 17.1 Hz, 1H), 3.85 (s, 3H), 3.69 (d, J = 17.4 Hz,1H). 3-114 (A) δ 7.86 (d, J = 8.1 Hz, 2H), 7.71 (d, J = 8.4 Hz, 2H),7.51 (bs, 2H), 7.4-7.45 (m, 2H), 7.08 (s, 1H), 6.98 (bs, 1H), 4.68 (d, J= 5.4 Hz, 2H), 4.07 (d, J = 17.4 Hz, 1H), 3.68 (d, J = 17.4 Hz, 1H),2.72 (s, 3H). 3-118 (D) δ 7.95-8.0 (m, 2H), 7.75-7.8 (m, 2H), 7.35-7.55(m, 4H), 5.45-5.5 (m, 2H), 4.15-4.2 (m, 1H), 3.8-3.85 (m, 1H), 2.57 (s,3H). 3-119 (B) δ 8.55-8.65 (m, 1H), 7.91 (d, J = 8.2 Hz, 2H), 7.65 (d, J= 8.2 Hz, 2H), 7.50 (s, 2H), 7.42 (s, 1H), 6.91 (s, 1H), 6.86 (s, 1H),4.67 (d, J = 5.3 Hz, 2H), 4.08 (d, J = 17.0 Hz, 1H), 3.77 (s, 3H), 3.70(d, J = 17.0 Hz, 1H). 3-120 (B) δ 7.35-8.0 (m, 8H), 6.95 (m, 2H),6.6-6.75 (m, 2H), 4.08 (d, J = 17.0 Hz, 1H), 3.70 (d, J = 17.0 Hz, 1H),3.63 (s, 3H). 3-121 (B) δ 8.1-8.2 (m, 1H), 7.65-7.9 (m, 3H), 7.4-7.6 (m,3H), 7.1-7.2 (m, 1H), 4.86 (d, J = 5.8 Hz, 2H), 4.05-4.15 (m, 1H),3.65-3.8 (m, 1H), 2.72 (s, 3H). 3-122 (A) δ 8.43 (s, 1H), 7.88 (d, J =8.1 Hz, 2H), 7.72 (d, J = 8.1 Hz, 2H), 7.51 (s, 2H), 7.44 (s, 1H), 7.30(t, J = 5.4 Hz, 1H), 4.93 (d, J = 5.4 Hz, 2H), 4.10 (d, J = 17.1 Hz,1H), 3.72 (d, J = 17.1 Hz, 1H). 3-127 (B) δ 7.93 (d, J = 8.2 Hz, 2H),7.82 (t, J = 4.8 Hz, 1H), 7.74 (d, J = 8.2 Hz, 2H), 7.58 (t, J = 7.7 Hz,1H), 7.5-7.55 (m, 2H), 7.43 (t, J = 1.8 Hz, 1H), 7.16 (d, J = 7.7 Hz,1H), 7.09 (d, J = 7.7 Hz, 1H), 4.71 (d, J = 4.8 Hz, 2H), 3.93 (d, J =17.2 Hz, 1H), 3.74 (d, J = 17.4 Hz, 1H), 2.57 (s, 3H). 3-131 (A) δ 8.55(s, 1H), 8.40 (s, 1H), 7.91 (d, J = 8.2 Hz, 2H), 7.72 (d, J = 8.2 Hz,2H), 7.53 (s, 3H), 7.42 (s, 1H), 4.7-4.8 (m, 2H), 4.13 (d, J = 17.0 Hz,1H), 3.74 (d, J = 17.0 Hz, 1H), 2.57 (s, 3H). 3-134 (A) δ 9.64 (bs, 1H),7.81 (d, J = 8.1 Hz, 2H), 7.69 (d, J = 8.1 Hz, 2H), 7.50 (s, 2H), 7.43(s, 1H), 4.10 (d, J = 17.4 Hz, 1H), 3.86 (s, 3H), 3.73 (d, J = 17.4 Hz,1H). 3-135 (A) δ 8.19 (d, J = 4.2 Hz, 1H), 7.95 (d, J = 8.4 Hz, 2H),7.76 (d, J = 8.4 Hz, 2H), 7.5-7.6 (m, 4H), 7.44 (s, 1H), 7.10 (bs, 1H),6.84 (t, J = 8.4 Hz, 1H), 6.78 (d, J = 8.4 Hz, 1H), 4.11 (d, J = 17.4Hz, 1H), 3.73 (d, J = 17.4 Hz, 1H). 3-143 (A) δ 8.57 (d, J = 5.1 Hz,1H), 8.21 (bs, 1H), 7.85-8.05 (m, 2H), 7.6-7.8 (m, 3H), 7.15-7.45 (m,5H), 4.72 (d, J = 5.1 Hz, 2H), 4.10 (d, J = 17.4 Hz, 1H), 3.76 (d, J =17.4 Hz, 1H), 2.38 (s, 3H). 3-147 (A) δ 7.86 (d, J = 8.5 Hz, 2H), 7.77(d, J = 8.5 Hz, 2H), 7.55-7.65 (m, 1H), 7.2-7.3 (m, 1H), 4.05-4.25 (m,3H), 3.86 (d, J = 17.0 Hz, 1H), 2.30 (s, 3H). 4-003 (A) δ 8.5-8.7 (m,1H), 7.35-7.9 (m, 9H), 7.1-7.3 (m, 1H), 4.5-5.1 (m, 4H), 4.0-4.2 (m,1H), 3.6-3.8 (m, 1H), 3.15-3.55 (m, 3H). 4-004 (A) δ 8.55-8.65 (m, 1H),7.35-7.8 (m, 9H), 7.1-7.3 (m, 1H), 4.6-5.15 (m, 4H), 3.3-4.2 (m, 4H),1.1-1.35 (m, 3H). 4-005 (A) δ 8.2-8.3 (m, 1H), 7.15-7.8 (m, 10H),4.75-5.35 (m, 4H), 4.08 (d, J = 17.0 Hz, 1H), 3.70 (d, J = 17.0 Hz, 1H),3.04 and 2.84 (bs, 3H). 4-006 (B) δ 8.5-8.6 (m, 1H), 7.1-7.75 (m, 10H),5.65-5.95 (m, 1H), 5.1-5.3 (m, 2H), 4.85 and 4.53 (s, 2H), 3.6-4.2 (m,4H). 4-007 (B) δ 8.5-8.7 (m, 1H), 6.95-7.75 (m, 10H), 5.65-6.1 (m, 2H),5.1-5.45 (m, 4H), 4.4-4.9 (m, 4H), 3.75-4.2 (m, 3H). 4-008 (A) δ 8.50(bs, 1H), 7.0-7.75 (m, 15H), 4.35-4.9 (m, 4H), 4.05 (d, J = 17.0 Hz,1H), 3.68 (d, J = 17.0 Hz, 1H). 4-009 (A) δ 8.5-8.55 (m, 1H), 7.65-7.75(m, 5H), 7.51 (s, 2H), 7.42 (s, 1H), 7.25-7.3 (m, 1H), 7.15-7.25 (m,1H), 5.17 (s, 2H), 4.10 (d, J = 17.0 Hz, 1H), 3.71 (d, J = 17.0 Hz, 1H),3.60 (s, 3H). 4-010 (A) δ 8.37 (bs, 1H), 7.65-7.8 (m, 3H), 7.3-7.55 (m,6H), 4.4-4.9 (m, 2H), 4.10 (d, J = 17.0 Hz, 1H), 3.70 (d, J = 17.0 Hz,1H), 3.1-3.65 (m, 2H), 1.12 (bs, 3H). 4-011 (B) δ 7.7-7.8 (m, 4H), 7.52(s, 2H), 7.43 (s, 1H), 4.10 (d, J = 17.0 Hz, 1H), 3.72 (d, J = 17.0 Hz,1H), 3.53 (s, 3H), 3.37 (s, 3H). 5-001 (A) δ 8.51 (d, J = 4.8 Hz, 1H),7.69 (t, J = 5.1 Hz, 1H), 7.62 (s, 1H), 7.45-7.55 (m, 2H), 7.25-7.4 (m,4H), 7.22 (dd, J = 6.9, 2.5 Hz, 1H), 4.73 (d, J = 5.1 Hz, 2H), 4.09 (d,J = 16.8 Hz, 1H), 3.73 (d, J = 16.8 Hz, 1H), 2.48 (s, 3H). 5-003 (A) δ8.51 (d, J = 4.8 Hz, 1H), 7.77 (s, 1H), 7.68 (t, J = 4.5 Hz, 1H),7.45-7.6 (m, 5H), 7.25-7.35 (m, 3H), 7.22 (dd, J = 7.5, 1.8 Hz, 1H),4.73 (d, J = 4.5 Hz, 2H), 4.09 (d, J = 17.4 Hz, 1H), 3.73 (d, J = 17.4Hz, 1H), 2.49 (s, 3H). 5-007 (A) δ 8.52 (d, J = 4.2 Hz, 1H), 7.78 (d, J= 9.3 Hz, 2H), 7.67 (t, J = 5.1 Hz, 1H), 7.51 (bs, 3H), 7.3-7.4 (m, 4H),7.15-7.25 (m, 1H), 4.73 (d, J = 5.1 Hz, 2H), 4.07 (d, J = 17.4 Hz, 1H),3.70 (d, J = 17.4 Hz, 1H), 2.48 (s, 3H). 5-009 (A) δ 8.51 (d, J = 4.5Hz, 1H), 7.89 (bs, 1H), 7.82 (d, J = 7.8 Hz, 1H), 7.65-7.75 (m, 2H),7.60 (t, J = 7.8 Hz, 1H), 7.5-7.55 (m, 3H), 7.33 (bs, 1H), 7.32 (d, J =7.8 Hz, 1H), 7.21 (dd, J = 7.2, 1.5 Hz, 1H), 4.73 (d, J = 5.1 Hz, 2H),4.15 (d, J = 17.4 Hz, 1H), 3.77 (d, J = 17.4 Hz, 1H), 2.49 (s, 3H).5-010 (A) δ 7.25-7.6 (m, 7H), 6.37 (bs, 1H), 4.0-4.15 (m, 2H), 4.11 (d,J = 17.4 Hz, 1H), 3.77 and 3.75 (d, J = 17.4 Hz, 1H), 2.95 (dd, J =10.2, 8.7 Hz, 1H), 2.41 (s, 3H), 2.03 (dd, J = 10.2, 3.3 Hz, 1H), 1.90(dd, J = 8.7, 3.3 Hz, 1H). 5-011 (A) δ 8.51 (d, J = 4.2 Hz, 1H), 7.69(t, J = 4.8 Hz, 1H), 7.15-7.6 (m, 10H), 4.72 (d, J = 4.8 Hz, 2H), 4.10(d, J = 17.1 Hz, 1H), 3.77 (dd, J = 17.1, 3.0 Hz, 1H), 2.95 (dd, J =10.2, 8.4 Hz, 1H), 2.48 (s, 3H), 2.02 (dd, J = 10.2, 3.0 Hz, 1H), 1.89(dd, J = 8.4, 3.0 Hz, 1H). 5-012 (A) δ 7.25-7.5 (m, 7H), 7.16 (bs, 1H),4.0-4.2 (m, 3H), 3.75 (d, J = 17.2 Hz, 1H), 2.42 (s, 3H). 5-013 (A) δ8.5-8.6 (m, 1H), 7.65-7.8 (m, 1H), 7.15-7.6 (m, 10H), 4.72 (d, J = 5.2Hz, 2H), 4.12 (d, J = 17.3 Hz, 1H), 3.74 (d, J = 17.3 Hz, 1H), 2.46 (s,3H). 5-015 (B) δ 8.5-8.55 (m, 1H), 7.72 (td, J = 6.8, 4.8 Hz, 1H),7.45-7.6 (m, 5H), 7.2-7.4 (m, 5H), 4.75 (d, J = 4.8 Hz, 2H), 4.11 (d, J= 17.2 Hz, 1H), 3.74 (d, J = 17.2 Hz, 1H), 2.50 (s, 3H). 5-016 (A) δ7.35-7.6 (m, 6H), 7.2-7.3 (m, 1H), 6.10 (d, J = 53.4 Hz, 1H), 6.06 (bs,1H), 4.0-4.2 (m, 3H), 3.72 (d, J = 16.8 Hz, 1H), 2.47 (s, 3H). 5-017 (A)δ 8.54 (d, J = 4.8 Hz, 1H), 7.65-7.75 (m, 1H), 7.35-7.6 (m, 6H),7.2-7.35 (m, 4H), 6.10 (d, J = 53.1 Hz, 1H), 4.75 (d, J = 5.1 Hz, 2H),4.11 (d, J = 17.4 Hz, 1H), 3.73 (d, J = 17.4 Hz, 1H), 2.50 (s, 3H).5-018 (A) δ 8.45-8.55 (m, 1H), 7.15-7.75 (m, 14H), 6.95-7.05 (m, 1H),5.19 (s, 2H), 4.74 (d, J = 4.4 Hz, 2H), 4.07 (d, J = 16.8 Hz, 1H), 3.75(d, J = 16.8 Hz, 1H), 2.49 (s, 3H). 5-019 (A) δ 8.24 (s, 1H), 8.00 (s,1H), 7.2-7.6 (m, 6H), 7.2-7.3 (m, 1H), 6.44 (t, J = 6.5 Hz, 1H),3.95-4.15 (m, 2H), 4.09 (d, J = 17.1 Hz, 1H), 3.78 (d, J = 17.1 Hz, 1H),2.40 (s, 3H). 5-020 (A) δ 8.52 (d, J = 4.8 Hz, 1H), 8.25 (s, 1H), 8.00(s, 1H), 7.45-7.75 (m, 7H), 7.15-7.35 (m, 4H), 4.74 (d, J = 4.8 Hz, 2H),4.10 (d, J = 17.4 Hz, 1H), 3.78 (d, J = 17.4 Hz, 1H), 2.49 (s, 3H).5-021 (A) δ 8.51 (d, J = 4.5 Hz, 1H), 7.69 (t, J = 5.1 Hz, 1H), 7.5-7.6(m, 4H), 7.25-7.4 (m, 5H), 7.21 (dd, J = 7.2, 1.5 Hz, 1H), 4.73 (d, J =5.1 Hz, 2H), 4.08 (d, J = 17.4 Hz, 1H), 3.74 (d, J = 17.4 Hz, 1H), 2.98(q, J = 7.2 Hz, 2H), 2.48 (s, 3H), 1.33 (t, J = 7.2 Hz, 3H). 5-022 (A) δ7.89 (s, 1H), 7.7-7.8 (m, 2H), 7.5-7.6 (m, 3H), 7.45 (d, J = 8.0 Hz,1H), 6.06 (t, J = 6.2 Hz, 1H), 4.0-4.2 (m, 3H), 3.73 (d, J = 16.6 Hz,1H), 2.47 (s, 3H). 5-023 (A) δ 8.55 (d, J = 4.7 Hz, 1H), 7.90 (s, 1H),7.65-7.8 (m, 3H), 7.5-7.6 (m, 4H), 7.3-7.45 (m, 2H), 7.2-7.3 (m, 1H),4.74 (d, J = 5.0 Hz, 2H), 4.12 (d, J = 17.1 Hz, 1H), 3.73 (d, J = 17.1Hz, 1H), 2.49 (s, 3H). 5-024 (B) δ 7.65 (d, J = 8.1 Hz, 1H), 7.45-7.6(m, 4H), 7.40 (d, J = 7.9 Hz, 1H), 7.34 (d, J = 7.7 Hz, 1H), 6.35 (bs,1H), 4.0-4.15 (m, 3H), 3.73 (d, J = 17.2 Hz, 1H), 3.37 (s, 3H), 2.43 (s,3H). 5-025 (B) δ 8.5-8.55 (m, 1H), 7.71 (td, J = 7.7, 1.6 Hz, 1H),7.3-7.7 (m, 7H), 7.28 (d, J = 4.6 Hz, 1H), 7.26 (t, J = 4.8 Hz, 1H),7.23 (dd, J = 7.5, 5.9 Hz, 1H), 4.75 (d, J = 4.8 Hz, 2H), 4.12 (d, J =17.2 Hz, 1H), 3.73 (d, J = 17.2 Hz, 1H), 3.39 (s, 3H), 2.50 (s, 3H).5-026 (B) δ 7.4-7.65 (m, 6H), 7.36 (d, J = 7.9 Hz, 1H), 6.34 (t, J = 6.1Hz, 1H), 4.11 (d, J = 17.2 Hz, 1H), 4.08 (qd, J = 9.6, 6.6 Hz, 2H), 3.73(d, J = 17.4 Hz, 1H), 3.50 (d, J = 0.9 Hz, 3H), 2.41 (s, 3H). 5-027 (B)δ 8.53 (ddd, J = 4.9, 1.6, 0.9 Hz, 1H), 7.70 (td, J = 7.7, 1.8 Hz, 1H),7.6-7.65 (m, 2H), 7.5-7.55 (m, 4H), 7.44 (ddd, J = 7.9, 2.0, 1.3 Hz,1H), 7.33 (d, J = 7.7 Hz, 1H), 7.26 (t, J = 4.8 Hz, 1H), 7.22 (ddd, J =7.5, 4.8, 1.1 Hz, 1H), 4.75 (d, J = 4.8 Hz, 2H), 4.12 (d, J = 17.2 Hz,1H), 3.74 (d, J = 17.2 Hz, 1H), 3.51 (s, 3H), 2.49 (s, 3H). 5-028 (B) δ8.5-8.55 (m, 1H), 7.83 (bs, 1H), 7.2-7.75 (m, 15H), 4.76 (d, J = 4.8 Hz,2H), 4.13 (dd, J = 17.2, 1.8 Hz, 1H), 3.82 (d, J = 17.2 Hz, 1H), 2.51(s, 3H). 5-029 (A) δ 8.51 (d, J = 4.5 Hz, 1H), 7.69 (t, J = 5.1 Hz, 1H),7.51 (bs, 2H), 7.50 (bs, 1H), 7.15-7.4 (m, 5H), 6.8-6.95 (m, 1H), 4.74(d, J = 4.8 Hz, 2H), 4.07 (d, J = 17.4 Hz, 1H), 3.72 (d, J = 17.4 Hz,1H), 2.48 (s, 3H). 5-030 (A) δ 7.2-7.45 (m, 6H), 6.49 (bs, 1H), 4.0-4.15(m, 2H), 3.46 (s, 2H), 2.40 (s, 3H), 1.79 (s, 3H). 5-031 (A) δ 7.25-7.5(m, 6H), 6.50 (bs, 1H), 4.0-4.15 (m, 2H), 3.60 (d, J = 16.8 Hz, 1H),3.39 (d, J = 16.8 Hz, 1H), 2.38 (s, 3H), 2.15-2.3 (m, 1H), 0.98 (d, J =6.6 Hz, 3H), 0.90 (d, J = 6.9 Hz, 3H). 5-033 (A) δ 8.51 (d, J = 4.8 Hz,1H), 7.69 (t, J = 4.5 Hz, 1H), 7.45-7.5 (m, 3H), 7.41 (bs, 2H), 7.15-7.4(m, 4H), 4.73 (d, J = 4.5 Hz, 2H), 3.57 (d, J = 16.8 Hz, 1H), 3.47 (d, J= 16.8 Hz, 1H), 2.48 (s, 3H), 1.35-1.5 (m, 1H), 0.45-0.7 (m, 4H). 5-035(B) δ 8.5-8.55 (m, 1H), 7.72 (td, J = 7.6, 1.8 Hz, 1H), 7.5-7.55 (m,4H), 7.43 (d, J = 1.8 Hz, 2H), 7.35-7.4 (m, 2H), 7.2-7.25 (m, 1H), 4.76(d, J = 4.8 Hz, 2H), 3.93 (d, J = 16.8 Hz, 1H), 3.85 (dd, J = 18.6, 11.8Hz, 2H), 3.53 (d, J = 16.8 Hz, 1H), 2.50 (s, 3H). 5-037 (A) δ 8.53 (d, J= 5.0 Hz, 1H), 7.65-7.75 (m, 1H), 7.15-7.6 (m, 9H), 5.89 (t, J = 55.2Hz, 1H), 4.74 (d, J = 4.7 Hz, 2H), 4.00 (d, J = 17.0 Hz, 1H), 3.55 (d, J= 17.0 Hz, 1H), 2.50 (s, 3H). 5-038 (B) δ 8.17 (t, J = 7.0 Hz, 1H),7.45-7.6 (m, 4H), 7.44 (t, J = 1.8 Hz, 1H), 7.0-7.1 (m, 1H), 4.05-4.25(m, 3H), 3.73 (d, J = 17.4 Hz, 1H). 5-040 (A) δ 8.82 (s, 1H), 8.19 (t, J= 7.8 Hz, 1H), 7.4-7.6 (m, 6H), 7.31 (s, 1H), 4.84 (d, J = 5.4 Hz, 2H),4.08 (d, J = 17.4 Hz, 1H), 3.69 (d, J = 17.1 Hz, 1H). 5-042 (B) δ 8.03(m, 1H), 7.64 (d, J = 1.1 Hz, 1H), 7.58 (d, J = 0.8 Hz, 1H), 7.50 (s,2H), 7.43 (bs, 1H), 6.39 (bs, 1H), 4.18 (d, J = 16.0 Hz, 1H), 4.1-4.2(m, 2H), 3.80 (d, J = 16.0 Hz, 1H). 5-048 (A) δ 8.22 (d, J = 8.7 Hz,2H), 7.81 (d, J = 7.8 Hz, 1H), 7.74 (d, J = 1.2 Hz, 1H), 7.63 (dd, J =8.4, 1.8 Hz, 1H), 7.54 (d, J = 8.7 Hz, 2H), 7.50 (bs, 2H), 7.44 (d, J =2.1 Hz, 1H), 6.72 (bs, 1H), 4.77 (d, J = 6.3 Hz, 2H), 4.04 (d, J = 17.1Hz, 1H), 3.66 (d, J = 17.1 Hz, 1H). 5-049 (A) δ 7.81 (d, J = 8.1 Hz,1H), 7.7-7.75 (m, 2H), 7.63 (dd, J = 8.1, 1.8 Hz, 1H), 7.50 (bs, 2H),7.44 (bs, 1H), 7.34 (d, J = 3.3 Hz, 1H), 7.16 (bs, 1H), 5.00 (d, J = 5.4Hz, 2H), 4.06 (d, J = 17.1 Hz, 1H), 3.69 (d, J = 17.1 Hz, 1H). 5-050 (A)δ 8.79 (s, 1H), 7.75 (dd, J = 8.4, 3.0 Hz, 1H), 7.70 (bs, 1H), 7.60 (bs,1H), 7.50 (bs, 2H), 7.44 (bs, 1H), 7.33 (s, 1H), 7.01 (bs, 1H), 4.82 (d,J = 5.1 Hz, 2H), 4.07 (d, J = 17.4 Hz, 1H), 3.69 (d, J = 17.1 Hz, 1H).5-051 (A) δ 7.7-7.8 (m, 2H), 7.61 (dd, J = 8.1, 1.5 Hz, 1H), 7.50 (bs,2H), 7.44 (bs, 1H), 7.19 (s, 1H), 6.84 (bs, 1H), 4.69 (d, J = 5.7 Hz,2H), 4.07 (d, J = 17.4 Hz, 1H), 3.69 (d, J = 17.4 Hz, 1H). 5-052 (B) δ8.63 (s, 1H), 7.25-7.75 (m, 7H), 5.10 (d, J = 5.8 Hz, 2H), 4.07 (d, J =17.0 Hz, 1H), 3.71 (d, J = 17.0 Hz, 1H). 5-053 (A) δ 8.54 (d, J = 4.2Hz, 1H), 7.77 (d, J = 7.8 Hz, 1H), 7.6-7.8 (m, 3H), 7.62 (d, J = 7.8 Hz,1H), 7.50 (bs, 2H), 7.44 (bs, 1H), 7.34 (d, J = 7.5 Hz, 1H), 7.23 (dd, J= 7.5, 2.4 Hz, 1H), 4.78 (d, J = 4.5 Hz, 2H), 4.08 (d, J = 18.0 Hz, 1H),3.71 (d, J = 18.0 Hz, 1H). 5-056 (A) δ 8.55 (d, J = 4.5 Hz, 1H), 8.08(t, J = 4.5 Hz, 1H), 7.96 (s, 1H), 7.78 (d, J = 8.4 Hz, 1H), 7.72 (d, J= 8.4 Hz, 1H), 7.69 (dd, J = 4.5, 2.4 Hz, 1H), 7.50 (bs, 2H), 7.43 (bs,1H), 7.33 (d, J = 7.2 Hz, 1H), 7.23 (dd, J = 7.2, 2.4 Hz, 1H), 4.73 (d,J = 4.5 Hz, 2H), 4.28 (d, J = 18.0 Hz, 1H), 3.87 (d, J = 18.0 Hz, 1H).5-058 (B) δ 8.54 (d, J = 3.9 Hz, 1H), 7.89 (bs, 1H), 7.74 (td, J = 7.8,1.8 Hz, 1H), 7.6-7.7 (m, 1H), 7.50 (bs, 3H), 7.44 (t, J = 1.8 Hz, 1H),7.38 (d, J = 7.8 Hz, 1H), 7.2-7.3 (bs, 1H), 4.79 (d, J = 4.7 Hz, 2H),4.07 (d, J = 17.2 Hz, 1H), 3.70 (d, J = 17.2 Hz, 1H). 5-060 (B) δ 8.01(bs, 1H), 7.65-7.75 (m, 2H), 7.50 (bs, 2H), 7.4-7.45 (m, 1H), 6.25-6.3(m, 1H), 4.06 (d, J = 17.2 Hz, 1H), 3.55-3.75 (m, 3H), 3.45-3.6 (m, 4H),1.20 (t, J = 7.0 Hz, 3H). 5-061 (B) δ 8.10 (bs, 1H), 7.69 (d, J = 8.0Hz, 1H), 7.50 (bs, 2H), 7.4-7.45 (m, 2H), 6.09 (bs, 1H), 4.54 (t, J =5.2 Hz, 1H), 4.06 (d, J = 17.2 Hz, 1H), 3.69 (d, J = 17.2 Hz, 1H), 3.60(t, J = 5.2 Hz, 2H), 3.44 (s, 6H). 5-062 (B) δ 8.13 (bs, 1H), 7.71 (d, J= 8.0 Hz, 1H), 7.4-7.5 (m, 4H), 6.7-6.9 (br, 1H), 6.05-6.3 (br, 1H),4.05-4.15 (m, 2H), 4.06 (d, J = 17.2 Hz, 1H), 3.69 (d, J = 17.2 Hz, 1H),2.88 (bs, 3H). 5-065 (B) δ 8.5-8.55 (m, 1H), 8.13 (d, J = 1.8 Hz, 1H),7.7-7.5 (m, 2H), 7.50 (d, J = 1.8 Hz, 2H), 7.44 (t, J = 1.8 Hz, 1H),7.37 (d, J = 8.0 Hz, 1H), 7.2-7.3 (m, 3H), 4.78 (d, J = 4.8 Hz, 2H),4.06 (d, J = 17.2 Hz, 1H), 3.68 (d, J = 17.2 Hz, 1H). 5-070 (A) δ7.35-7.55 (m, 6H), 6.02 (bs, 1H), 4.09 (d, J = 17.4 Hz, 1H), 3.71 (d, J= 17.4 Hz, 1H), 3.25-3.35 (m, 2H), 2.45 (s, 3H), 1.0-1.15 (m, 1H),0.55-0.65 (m, 2H), 0.25-0.35 (m, 2H). 5-072 (A) δ 7.35-7.55 (m, 6H),5.78 (bs, 1H), 4.08 (d, J = 17.0 Hz, 1H), 3.69 (d, J = 17.0 Hz, 1H),3.47 (t, J = 7.1 Hz, 2H), 2.45-2.65 (m, 1H), 2.44 (s, 3H), 1.65-2.2 (m,6H). 5-077 (A) δ 7.4-7.5 (m, 6H), 6.19 (bs, 1H), 4.08 (d, J = 16.8 Hz,1H), 3.5-3.75 (m, 7H), 2.47 (s, 3H), 1.20 (t, J = 6.9 Hz, 3H). 5-079 (B)δ 7.45-7.55 (m, 4H), 7.43 (t, J = 1.8 Hz, 1H), 7.39 (d, J = 8.4 Hz, 1H),6.28 (bs, 1H), 4.27 (t, J = 5.1 Hz, 2H), 4.08 (d, J = 17.2 Hz, 1H),3.65-3.75 (m, 3H), 2.44 (s, 3H), 2.08 (s, 3H). 5-080 (B) δ 7.45-7.55 (m,4H), 7.35-7.45 (m, 2H), 6.48 (bs, 1H), 4.80 (bs, 1H), 4.28 (t, J = 5.0Hz, 2H), 4.08 (d, J = 17.2 Hz, 1H), 3.70 (d, J = 17.2 Hz, 1H), 3.65-3.7(m, 2H), 3.15-3.25 (m, 2H), 2.46 (s, 3H), 1.13 (t, J = 7.2 Hz, 3H).5-083 (A) δ 7.4-7.55 (m, 6H), 5.95 (bs, 1H), 4.48 (t, J = 5.4 Hz, 1H),4.05 (d, J = 17.4 Hz, 1H), 3.66 (d, J = 17.4 Hz, 1H), 3.59 (t, J = 5.4Hz, 2H), 3.44 (s, 6H), 2.48 (s, 3H). 5-084 (A) δ 7.4-7.55 (m, 6H), 6.02(bs, 1H), 4.63 (t, J = 5.1 Hz, 1H), 4.08 (d, J = 16.8 Hz, 1H), 3.5-3.8(m, 7H), 2.48 (s, 3H), 1.22 (t, J = 6.6 Hz, 6H). 5-085 (B) δ 7.45-7.55(m, 4H), 7.43 (t, J = 1.8 Hz, 1H), 7.39 (d, J = 8.4 Hz, 1H), 6.31 (d, J= 8.1 Hz, 1H), 4.81 (bs, 1H), 4.35-4.45 (m, 1H), 4.22 (dd, J = 11.5, 6.8Hz, 1H), 4.10 (dd, J = 11.5, 3.7 Hz, 1H), 4.08 (d, J = 17.2 Hz, 1H),3.70 (d, J = 17.2 Hz, 1H), 3.15-3.25 (m, 2H), 2.45 (s, 3H), 1.27 (d, J =7.1 Hz, 3H), 1.13 (t, J = 7.2 Hz, 3H). 5-086 (A) δ 7.35-7.6 (m, 6H),6.24 (bs, 1H), 4.0-4.15 (m, 2H), 3.65-3.9 (m, 4H), 3.25-3.35 (m, 1H),2.46 (s, 3H), 1.85-2.1 (m, 3H), 1.55-1.7 (m, 1H). 5-087 (A) δ 7.35-7.55(m, 6H), 5.97 (bs, 1H), 4.08 (d, J = 17.4 Hz, 1H), 3.55-4.0 (m, 4H),3.69 (d, J = 17.1 Hz, 1H), 3.45-3.5 (m, 2H), 2.55-2.65 (m, 1H), 2.47 (s,3H), 2.05-2.15 (m, 1H), 1.6-1.75 (m, 1H). 5-090 (A) δ 7.4-7.55 (m, 6H),6.14 (bs, 1H), 4.75 (t, J = 4.5 Hz, 1H), 4.1-4.2 (m, 2H), 4.08 (d, J =17.4 Hz, 1H), 3.75-3.9 (m, 2H), 3.71 (d, J = 17.4 Hz, 1H), 3.5-3.65 (m,2H), 2.47 (s, 3H), 2.0-2.15 (m, 1H), 1.3-1.45 (m, 1H). 5-092 (A) δ7.35-7.6 (m, 6H), 7.05 (bs, 1H), 4.08 (d, J = 17.1 Hz, 1H), 3.9-4.05 (m,2H), 3.70 (d, J = 17.1 Hz, 1H), 3.1-3.25 (m, 1H), 2.8-2.95 (m, 1H), 2.66(s, 3H), 2.47 (s, 3H). 5-094 (A) δ 7.4-7.6 (m, 6H), 6.73 (bs, 1H), 4.08(d, J = 17.1 Hz, 1H), 3.9-4.05 (m, 2H), 3.70 (d, J = 17.1 Hz, 1H), 3.28(t, J = 5.7 Hz, 2H), 3.08 (q, J = 7.5 Hz, 2H), 2.47 (s, 3H), 1.43 (t, J= 7.5 Hz, 3H). 5-095 (A) δ 7.2-7.6 (m, 11H), 6.09 (bs, 1H), 4.08 (d, J =17.1 Hz, 1H), 3.75 (s, 2H), 3.70 (d, J = 17.1 Hz, 1H), 3.5-3.6 (m, 2H),2.68 (t, J = 6.3 Hz, 2H), 2.45 (s, 3H). 5-096 (A) δ 7.35-7.55 (m, 11H),6.62 (t, J = 6.0 Hz, 1H), 4.30 (s, 2H), 4.07 (d, J = 17.4 Hz, 1H),3.85-3.95 (m, 2H), 3.69 (d, J = 17.4 Hz, 1H), 3.1-3.2 (m, 2H), 2.41 (s,3H). 5-097 (A) δ 7.35-7.55 (m, 6H), 7.32 (s, 1H), 6.30 (bs, 1H), 6.22(d, J = 2.7 Hz, 1H), 6.13 (bs, 1H), 4.08 (d, J = 17.4 Hz, 1H), 3.77 (s,2H), 3.70 (d, J = 17.4 Hz, 1H), 3.55-3.65 (m, 2H), 2.78 (t, J = 6.3 Hz,2H), 2.47 (s, 3H). 5-098 (A) δ 7.4-7.55 (m, 7H), 6.55-6.6 (m, 2H), 6.45(dd, J = 3.0, 1.8 Hz, 1H), 4.39 (s, 2H), 4.07 (d, J = 17.4 Hz, 1H),3.85-3.95 (m, 2H), 3.69 (d, J = 17.4 Hz, 1H), 3.25-3.3 (m, 2H), 2.45 (s,3H). 5-099 (A) δ 7.4-7.6 (m, 6H), 6.22 (t, J = 5.4 Hz, 1H), 4.08 (d, J =17.0 Hz, 1H), 3.6-3.75 (m, 2H), 3.35-3.5 (m, 1H), 2.85-3.05 (m, 1H),2.49 (s, 3H), 2.11 (s, 3H), 1.35 (d, J = 6.9 Hz, 3H). 5-100 (A) δ7.4-7.6 (m, 6H), 7.15-7.25 and 6.9-7.0 (m, 1H), 3.9-4.2 (m, 2H),3.6-3.85 (m, 2H), 2.85-3.2 (m, 1H), 2.68 and 2.56 (s, 3H), 2.49 (s, 3H),1.32 (d, J = 6.9 Hz, 3H). 5-101 (A) δ 7.4-7.6 (m, 6H), 6.65 (t, J = 5.8Hz, 1H), 4.08 (d, J = 17.3 Hz, 1H), 3.75-4.0 (m, 2H), 3.69 (d, J = 17.3Hz, 1H), 3.25-3.45 (m, 1H), 2.94 (s, 3H), 2.49 (s, 3H), 1.50 (d, J = 6.9Hz, 3H). 5-102 (A) δ 7.35-7.65 (m, 6H), 6.08 (bs, 1H), 4.3-4.45 (m, 1H),4.09 (d, J = 17.4 Hz, 1H), 3.71 (d, J = 17.4 Hz, 1H), 2.71 (d, J = 5.7Hz, 2H), 2.44 (s, 3H), 2.17 (s, 3H), 1.34 (d, J = 6.6 Hz, 3H). 5-103 (A)δ 7.4-7.6 (m, 6H), 6.46 (d, J = 8.1 Hz, 1H), 4.6-4.75 (m, 1H), 4.08 (d,J = 17.1 Hz, 1H), 3.70 (d, J = 17.4 Hz, 1H), 3.42 (dd, J = 14.4, 6.3 Hz,1H), 3.26 (dd, J = 14.4, 5.1 Hz, 1H), 3.03 (s, 3H), 2.45 (s, 3H), 1.53(d, J = 6.9 Hz, 3H). 5-104 (A) δ 7.45-7.55 (m, 4H), 7.4-7.45 (m, 2H),5.75 (bs, 1H), 4.07 (d, J = 17.4 Hz, 1H), 3.69 (d, J = 17.4 Hz, 1H),3.07 (s, 2H), 2.48 (s, 3H), 2.18 (s, 3H), 1.51 (s, 6H). 5-112 (A) δ7.45-7.65 (m, 6H), 7.43 and 6.93 (t, J = 4.8 Hz, 1H), 6.29 (bs, 1H),4.33 and 4.25 (t, J = 4.7 Hz, 2H), 4.08 (d, J = 17.1 Hz, 1H), 3.70 (d, J= 17.4 Hz, 1H), 2.48 (s, 3H). 5-114 (A) δ 7.4-7.6 (m, 6H), 7.43 and 6.85(bs, 1H), 6.30 (bs, 1H), 4.25-4.35 and 4.2-4.25 (m, 2H), 4.08 (d, J =17.4 Hz, 1H), 3.93 and 3.86 (d, J = 7.2 Hz, 2H), 3.70 (d, J = 17.4 Hz,1H), 2.49 (s, 3H), 1.1-1.3 (m, 1H), 0.5-0.6 (m, 2H), 0.2-0.3 (m, 2H).5-115 (A) δ 7.57 and 6.86 (t, J = 4.4 Hz, 1H), 7.25-7.55 (m, 10H), 6.26(bs, 1H), 5.10 and 5.02 (s, 2H), 4.28 and 4.20 (t, J = 5.3 Hz, 2H), 4.08(d, J = 17.1 Hz, 1H), 3.70 (d, J = 17.1 Hz, 1H), 2.44 (s, 3H). 5-116 (A)δ 7.4-7.5 (m, 6H), 7.39 and 6.79 (t, J = 4.5 Hz, 1H), 6.25 and 6.15 (bs,1H), 4.0-4.3 (m, 4H), 4.05 (d, J = 17.4 Hz, 1H), 3.67 (d, J = 17.4 Hz,1H), 2.46 and 2.45 (s, 3H), 0.9-1.25 (m, 2H), 0.01 (s, 9H). 5-118 (A) δ7.45-7.55 (m, 4H), 7.35-7.45 (m, 2H), 6.19 (bs, 1H), 4.7-4.85 (m, 1H),4.08 (d, J = 17.4 Hz, 1H), 3.7-3.8 (m, 1H), 3.70 (d, J = 17.4 Hz, 1H),3.5-3.6 (m, 1H), 3.0-3.15 (m, 1H), 2.7-2.85 (m, 1H), 2.47 (s, 3H), 2.00(s, 3H). 5-120 (A) δ 7.4-7.6 (m, 6H), 7.11 (d, J = 9.6 Hz, 1H), 6.30 (d,J = 9.6 Hz, 1H), 4.0-4.25 (m, 3H), 3.70 (d, J = 17.0 Hz, 1H), 2.50 (s,3H). 5-122 (A) δ 7.4-7.6 (m, 7H), 6.61 (d, J = 3.3 Hz, 1H), 6.49 (d, J =8.4 Hz, 1H), 6.44 (dd, J = 3.3, 2.1 Hz, 1H), 6.33 (d, J = 8.4 Hz, 1H),4.08 (d, J = 17.3 Hz, 1H), 3.70 (d, J = 17.3 Hz, 1H), 2.48 (s, 3H).5-123 (A) δ 7.3-7.6 (m, 8H), 7.0-7.1 (m, 1H), 6.49 (d, J = 8.8 Hz, 1H),6.42 (d, J = 8.8 Hz, 1H), 4.08 (d, J = 17.0 Hz, 1H), 3.69 (d, J = 17.0Hz, 1H), 2.50 (s, 3H). 5-126 (A) δ 8.62 (d, J = 5.0 Hz, 1H), 7.85 (td, J= 8.1, 2.1 Hz, 1H), 7.35-7.65 (m, 9H), 6.15 (d, J = 6.9 Hz, 1H), 4.09(d, J = 17.0 Hz, 1H), 3.71 (d, J = 17.0 Hz, 1H), 2.52 (s, 3H). 5-128 (A)δ 7.45-7.65 (m, 6H), 6.33 (bs, 1H), 4.23 (d, J = 5.1 Hz, 2H), 4.09 (d, J= 17.4 Hz, 1H), 3.81 (s, 3H), 3.70 (d, J = 17.4 Hz, 1H), 2.49 (s, 3H).5-130 (B) δ 7.4-7.55 (m, 6H), 6.33 (d, J = 6.6 Hz, 1H), 4.75-4.85 (m,1H), 4.08 (d, J = 17.2 Hz, 1H), 3.81 (s, 3H), 3.70 (d, J = 17.2 Hz, 1H),2.49 (s, 3H), 1.55 (s, 3H). 5-131 (B) δ 7.4-7.55 (m, 6H), 6.34 (d, J =7.6 Hz, 1H), 4.7-4.8 (m, 1H), 4.2-4.3 (m, 2H), 4.08 (d, J = 17.4 Hz,1H), 3.70 (d, J = 17.4 Hz, 1H), 2.49 (s, 3H), 1.54 (t, J = 7.0 Hz, 3H),1.32 (t, J = 7.2 Hz, 3H). 5-132 (A) δ 7.4-7.55 (m, 6H), 6.36 (bs, 1H),4.75-4.9 (m, 1H), 4.6-4.75 (m, 1H), 4.4-4.55 (m, 1H), 4.18 (d, J = 17.4Hz, 1H), 3.71 (d, J = 17.4 Hz, 1H), 2.45 (s, 3H), 1.57 (d, J = 7.2 Hz,3H). 5-133 (A) δ 7.4-7.6 (m, 6H), 7.06 (d, J = 6.6 Hz, 1H), 5.76 (t, J =6.6 Hz, 1H), 4.27 (d, J = 6.6 Hz, 1H), 4.08 (d, J = 17.1 Hz, 1H), 3.89(s, 3H), 3.70 (d, J = 17.1 Hz, 1H), 2.49 (s, 3H). 5-134 (A) δ 7.4-7.6(m, 6H), 6.79 (d, J = 9.4 Hz, 1H), 5.72 (d, J = 9.4 Hz, 1H), 4.09 (d, J= 17.3 Hz, 1H), 3.87 (s, 3H), 3.71 (d, J = 17.3 Hz, 1H), 3.59 (s, 3H),2.51 (s, 3H). 5-136 (A) δ 7.35-7.55 (m, 6H), 6.44 (bs, 1H), 4.05-4.25(m, 3H), 3.6-3.8 (m, 3H), 2.66 (t, J = 6.0 Hz, 2H), 2.46 (s, 3H), 1.27(t, J = 7.2 Hz, 3H). 5-138 (A) δ 7.45-7.6 (m, 6H), 7.09 (bs, 1H), 6.69(bs, 1H), 4.05-4.15 (m, 3H), 3.72 (d, J = 17.4 Hz, 1H), 2.83 (d, J = 4.8Hz, 3H), 2.44 (s, 3H). 5-139 (A) δ 7.5-7.6 (m, 5H), 7.43 (s, 1H), 6.98(bs, 1H), 4.23 (d, J = 3.9 Hz, 2H), 4.09 (d, J = 17.1 Hz, 1H), 3.71 (d,J = 17.1 Hz, 1H), 3.04 (s, 3H), 3.02 (s, 3H), 2.50 (s, 3H). 5-141 (B) δ7.4-7.55 (m, 6H), 7.05-7.1 (m, 1H), 6.62 (bs, 1H), 4.05-4.15 (m, 3H),3.72 (d, J = 17.2 Hz, 1H), 3.23 (dd, J = 13.8, 7.2 Hz, 2H), 2.45 (s,3H), 1.5-1.6 (m, 2H), 0.91 (t, J = 7.4 Hz, 3H). 5-143 (B) δ 7.4-7.55 (m,6H), 6.9-7.05 (m, 1H), 6.45-6.55 (m, 1H), 4.05-4.2 (m, 3H), 3.70 (d, J =17.2 Hz, 1H), 3.1-3.15 (m, 2H), 2.45-2.5 (m, 4H), 0.9-1.0 (m, 6H). 5-145(B) δ 7.4-7.55 (m, 6H), 6.78 (bs, 1H), 5.93 (bs, 1H), 4.0-4.15 (m, 3H),3.70 (d, J = 16.8 Hz, 1H), 2.48 (s, 3H), 1.38 (s, 9H). 5-146 (B) δ7.4-7.55 (m, 6H), 7.01 (bs, 1H), 6.53 (bs, 1H), 4.05-4.2 (m, 3H), 3.71(d, J = 17.4 Hz, 1H), 3.05-3.1 (m, 2H), 2.46 (s, 3H), 0.91 (s, 9H).5-147 (B) δ 7.4-7.55 (m, 6H), 6.89 (bs, 2H), 4.56 (t, J = 5.0 Hz, 1H),4.44 (t, J = 5.0 Hz, 1H), 4.16 (d, J = 5.0 Hz, 2H), 4.19 (d, J = 17.2Hz, 1H), 3.71 (d, J = 17.2 Hz, 1H), 3.5-3.7 (m, 2H), 2.46 (s, 3H). 5-149(A) δ 7.45-7.6 (m, 5H), 7.42 (s, 1H), 7.27 (bs, 1H), 4.25-4.4 (m, 2H),4.09 (d, J = 17.4 Hz, 1H), 3.6-3.8 (m, 5H), 3.17 (s, 3H), 2.49 (s, 3H).5-150 (B) δ 7.4-7.55 (m, 6H), 6.8-7.2 (m, 2H), 4.16 (d, J = 5.0 Hz, 2H),4.09 (d, J = 17.2 Hz, 1H), 3.5-3.75 (m, 3H), 3.48 (t, J = 5.8 Hz, 2H),2.48 (s, 3H). 5-152 (A) δ 7.4-7.55 (m, 6H), 7.05 (bs, 1H), 6.90 (bs,1H), 4.0-4.2 (m, 3H), 3.71 (d, J = 17.0 Hz, 1H), 3.5-3.6 (m, 2H),3.4-3.5 (m, 2H), 2.45 (s, 3H), 1.9-2.1 (m, 2H). 5-153 (B) δ 7.4-7.55 (m,6H), 6.7-7.05 (m, 2H), 4.15-4.2 (m, 2H), 4.09 (d, J = 17.2 Hz, 1H),3.75-3.9 (m, 1H), 3.71 (d, J = 17.2 Hz, 1H), 3.05-3.2 (m, 1H), 2.47 (s,3H), 1.49 (bs, 1H), 1.6-1.7 (m, 1H), 1.2-1.3 (m, 1H). 5-154 (A) δ7.45-7.55 (m, 5H), 7.43 (s, 1H), 6.86 (bs, 1H), 6.77 (bs, 1H), 4.05-4.15(m, 3H), 3.65-3.8 (m, 3H), 3.45-3.55 (m, 2H), 2.46 (s, 3H), 1.69 (bs,1H). 5-155 (B) δ 7.5-7.55 (m, 5H), 7.43 (t, J = 1.8 Hz, 1H), 6.9-7.0 (m,1H), 4.25-4.4 (m, 2H), 4.19 (d, J = 17.4 Hz, 1H), 3.8-3.9 (m, 2H), 3.70(d, J = 17.4 Hz, 1H), 3.63 (t, J = 5.2 Hz, 1H), 3.49 (t, J = 5.2 Hz,1H), 3.13 and 3.04 (s, 3H), 2.50 (s, 3H). 5-159 (B) δ 7.4-7.55 (m, 6H),7.25-7.35 (m, 1H), 7.0-7.05 (m, 1H), 4.10 (d, J = 17.2 Hz, 1H), 4.06(bs, 2H), 3.77 (bs, 2H), 3.73 (d, J = 17.2 Hz, 1H), 3.25 (t, J = 5.6 Hz,2H), 2.96 (s, 3H), 2.42 (s, 3H). 5-161 (B) δ 7.4-7.55 (m, 6H), 6.96 (bs,1H), 5.7-5.85 (m, 1H), 5.15-5.35 (m, 2H), 4.2-4.3 (m, 2H), 4.05-4.15 (m,2H), 3.92 (bs, 1H), 3.71 (d, J = 17.2 Hz, 1H), 3.01 and 2.99 (s, 3H),2.50 (s, 3H). 5-162 (B) δ 7.45-7.55 (m, 5H), 7.4-7.45 (m, 1H), 6.97 (bs,1H), 5.7-5.85 (m, 2H), 5.15-5.3 (m, 4H), 4.27 (d, J = 4.0 Hz, 2H), 4.10(d, J = 17.2 Hz, 1H), 4.05 (d, J = 5.8 Hz, 2H), 3.91 (d, J = 5.8 Hz,2H), 3.72 (d, J = 17.2 Hz, 1H), 2.50 (s, 3H). 5-163 (A) δ 7.4-7.6 (m,6H), 6.9-7.2 (m, 2H), 5.38 (s, 1H), 5.30 (s, 1H), 4.0-4.3 (m, 5H), 3.70(d, J = 17.0 Hz, 1H), 2.44 (s, 3H). 5-165 (B) δ 7.4-7.55 (m, 6H), 7.00(bs, 2H), 4.05-4.2 (m, 5H), 3.72 (d, J = 17.2 Hz, 1H), 2.54 (s, 3H),2.22 (s, 1H). 5-167 (B) δ 8.78 (d, J = 1.8 Hz, 1H), 7.45-7.55 (m, 6H),7.43 (t, J = 1.8 Hz, 1H), 6.65-6.8 (m, 2H), 4.65 (d, J = 7.4 Hz, 2H),4.05-4.2 (m, 3H), 3.70 (d, J = 17.2 Hz, 1H), 2.46 (s, 3H). 5-168 (B) δ8.52 (d, J = 4.1 Hz, 1H), 7.67 (td, J = 7.8, 1.8 Hz, 1H), 7.4-7.55 (m,8H), 7.2-7.25 (m, 1H), 6.83 (bs, 1H), 4.59 (d, J = 5.0 Hz, 2H), 4.22 (d,J = 5.0 Hz, 2H), 4.08 (d, J = 17.2 Hz, 1H), 3.70 (d, J = 17.2 Hz, 1H),2.47 (s, 3H). 5-171 (B) δ 7.45-7.55 (m, 6H), 6.94 (bs, 1H), 4.25 (d, J =3.8 Hz, 2H), 4.08 (d, J = 17.2 Hz, 1H), 3.65-3.75 (m, 7H), 3.48 (t, J =4.4 Hz, 2H), 2.50 (s, 3H). 5-173 (B) δ 7.2-7.6 (m, 7H), 6.6-7.1 (m, 6H),4.0-4.6 (m, 3H), 3.70 (d, J = 17.0 Hz, 1H), 3.33 (s, 3H), 2.49 (s, 3H).5-176 (B) δ 7.3-7.55 (m, 12H), 6.37 (bs, 1H), 5.71 (d, J = 7.0 Hz, 1H),4.08 (d, J = 17.2 Hz, 1H), 3.71 (d, J = 17.2 Hz, 1H), 2.75 (d, J = 4.9Hz, 3H), 2.41 (s, 3H). 5-178 (A) δ 7.45-7.6 (m, 5H), 7.43 (s, 1H), 6.62(bs, 1H), 4.37 (t, J = 9.3 Hz, 2H), 4.23 (d, J = 4.5 Hz, 2H), 4.09 (d, J= 17.1 Hz, 1H), 3.86 (t, J = 9.3 Hz, 2H), 3.71 (d, J = 17.1 Hz, 1H),2.48 (s, 3H). 5-179 (A) δ 8.10 (bs, 1H), 7.4-7.65 (m, 7H), 7.06 (bs,1H), 4.43 (d, J = 5.1 Hz, 2H), 4.09 (d, J = 17.1 Hz, 1H), 3.71 (d, J =17.1 Hz, 1H), 2.49 (s, 3H). 5-180 (A) δ 7.65-7.8 (m, 2H), 7.1-7.6 (m,12H), 6.03 (d, J = 7.4 Hz, 1H), 4.08 (d, J = 17.0 Hz, 1H), 3.70 (d, J =17.0 Hz, 1H), 2.45 (s, 3H). 5-181 (A) δ 7.51 (bs, 4H), 7.4-7.45 (m, 1H),7.38 (d, J = 8.5 Hz, 1H), 5.5-5.6 (m, 1H), 4.08 (d, J = 17.1 Hz, 1H),3.69 (d, J = 17.1 Hz, 1H), 2.97 (d, J = 6.1 Hz, 2H), 2.46 (s, 3H), 0.13(s, 9H). 5-182 (A) δ 7.51 (bs, 4H), 7.4-7.45 (m, 2H), 5.85-6.05 (m, 1H),5.81 (bs, 1H), 5.15-5.35 (m, 2H), 4.05-4.15 (m, 3H), 3.69 (d, J = 17.4Hz, 1H), 2.49 (s, 3H). 5-183 (A) δ 7.4-7.75 (m, 5H), 7.33 (d, J = 7.8Hz, 1H), 4.04 (d, J = 17.1 Hz, 1H), 3.75 (m, 1H), 3.66 (d, J = 17.4 Hz,1H), 3.37 (m, 1H), 3.08 (m, 2H), 1.25 (t, J = 7.4 Hz, 3H), 1.04 (t, J =7.2 Hz, 3H). 5-184 (A) δ 7.51 (bs, 4H), 7.4-7.5 (m, 2H), 6.10 (t, J =6.9 Hz, 1H), 5.95 (bs, 1H), 4.17 (t, J = 6.6 Hz, 2H), 4.08 (d, J = 17.1Hz, 1H), 3.69 (d, J = 17.4 Hz, 1H), 2.48 (s, 3H). 5-185 (A) δ 7.4-7.55(m, 6H), 6.58 and 6.34 (s, 1H), 6.10 and 5.99 (bs, 1H), 4.49 and 4.30(d, J = 6.0 Hz, 2H), 4.08 (d, J = 17.1 Hz, 1H), 3.69 (d, J = 17.1 Hz,1H), 2.50 and 2.48 (s, 3H). 5-186 (A) δ 7.35-7.55 (m, 6H), 6.03 (bs,1H), 4.27 (q, J = 2.4 Hz, 2H), 4.08 (d, J = 17.4 Hz, 1H), 3.70 (d, J =17.4 Hz, 1H), 2.47 (s, 3H), 2.30 (t, J = 2.4 Hz, 1H). 5-189 (A) δ7.25-7.55 (m, 11H), 6.0-6.2 (m, 1H), 5.2-5.4 (m, 1H), 4.06 (d, J = 17.3Hz, 1H), 3.68 (d, J = 17.3 Hz, 1H), 2.41 (s, 3H), 1.60 (d, J = 6.9 Hz,3H). 5-191 (A) δ 7.2-7.6 (m, 11H), 6.09 (bs, 1H), 5.06 (q, J = 7.5 Hz,1H), 4.06 (d, J = 17.1 Hz, 1H), 3.68 (d, J = 17.1 Hz, 1H), 2.40 (s, 3H),1.85-2.0 (m, 2H), 0.97 (t, J = 7.2 Hz, 3H). 5-194 (B) δ 7.3-7.6 (m,11H), 6.42 (d, J = 9.6 Hz, 1H), 6.26 (d, J = 9.6 Hz, 1H), 4.07 (d, J =17.2 Hz, 1H), 3.85-3.95 (m, 1H), 3.7-3.8 (m, 1H), 3.69 (d, J = 17.2 Hz,1H), 2.50 (s, 3H), 1.33 (t, J = 7.2 Hz, 3H). 5-205 (A) δ 7.35-7.55 (m,7H), 6.25-6.35 (m, 2H), 6.10 (bs, 1H), 4.62 (d, J = 5.4 Hz, 2H), 4.07(d, J = 17.1 Hz, 1H), 3.69 (d, J = 17.1 Hz, 1H), 2.46 (s, 3H). 5-207 (A)δ 7.3-7.55 (m, 6H), 6.7-6.8 (m, 2H), 6.39 (bs, 1H), 4.64 (d, J = 6.0 Hz,2H), 4.07 (d, J = 17.4 Hz, 1H), 3.69 (d, J = 17.4 Hz, 1H), 2.43 (s, 3H).5-208 (A) δ 7.4-7.6 (m, 6H), 6.37 (bs, 1H), 6.04 (s, 1H), 4.66 (d, J =5.7 Hz, 2H), 4.08 (d, J = 17.4 Hz, 1H), 3.69 (d, J = 17.4 Hz, 1H), 2.49(s, 3H), 2.43 (s, 3H). 5-209 (A) δ 7.35-7.6 (m, 6H), 6.57 (t, J = 6.0Hz, 1H), 6.31 (s, 1H), 4.70 (d, J = 6.0 Hz, 2H), 4.09 (d, J = 17.4 Hz,1H), 3.71 (d, J = 17.4 Hz, 1H), 2.43 (s, 3H). 5-212 (A) δ 7.56 (s, 1H),7.35-7.55 (m, 6H), 5.90 (bs, 1H), 4.46 (d, J = 5.4 Hz, 2H), 4.07 (d, J =17.1 Hz, 1H), 3.85 (s, 3H), 3.68 (d, J = 17.1 Hz, 1H), 2.47 (s, 3H).5-213 (A) δ 7.3-7.55 (m, 6H), 6.19 (bs, 1H), 4.43 (d, J = 5.4 Hz, 2H),4.07 (d, J = 17.4 Hz, 1H), 3.78 (s, 3H), 3.72 (d, J = 17.1 Hz, 1H), 2.43(s, 3H). 5-216 (A) δ 7.74 (d, J = 3.3 Hz, 1H), 7.45-7.55 (m, 5H), 7.43(bs, 1H), 7.40 (d, J = 3.3 Hz, 1H), 6.66 (bs, 1H), 4.95 (d, J = 5.4 Hz,2H), 4.08 (d, J = 16.8 Hz, 1H), 3.70 (d, J = 17.4 Hz, 1H), 2.50 (s, 3H).5-217 (A) δ 7.75 (d, J = 3.3 Hz, 1H), 7.3-7.6 (m, 13H), 6.59 (d, J = 7.4Hz, 1H), 4.08 (d, J = 17.3 Hz, 1H), 3.69 (d, J = 17.3 Hz, 1H), 2.46 (s,3H). 5-218 (A) δ 7.76 (s, 1H), 7.4-7.75 (m, 6H), 6.78 (bs, 1H), 4.93 (d,J = 3.6 Hz, 2H), 4.09 (d, J = 17.4 Hz, 1H), 3.70 (d, J = 17.4 Hz, 1H),2.47 (s, 3H). 5-220 (A) δ 7.4-7.55 (m, 6H), 7.17 (s, 1H), 6.40 (bs, 1H),4.64 (d, J = 5.7 Hz, 2H), 4.08 (d, J = 17.1 Hz, 1H), 3.73 (d, J = 17.1Hz, 1H), 2.46 (s, 3H). 5-221 (A) δ 7.4-7.55 (m, 6H), 7.07 (s, 1H), 6.42(bs, 1H), 4.66 (d, J = 5.4 Hz, 2H), 4.05 (d, J = 17.4 Hz, 1H), 3.66 (d,J = 17.4 Hz, 1H), 2.70 (s, 3H), 2.47 (s, 3H). 5-222 (A) δ 8.76 (s, 1H),7.81 (s, 1H), 7.50 (bs, 4H), 7.35-7.45 (m, 2H), 6.36 (bs, 1H), 4.83 (d,J = 6.0 Hz, 2H), 4.07 (d, J = 17.4 Hz, 1H), 3.69 (d, J = 17.1 Hz, 1H),2.46 (s, 3H). 5-223 (A) δ 7.45-7.55 (m, 4H), 7.35-7.45 (m, 3H), 6.27 (t,J = 6.0 Hz, 1H), 4.71 (d, J = 6.0 Hz, 2H), 4.08 (d, J = 17.4 Hz, 1H),3.69 (d, J = 17.4 Hz, 1H), 2.48 (s, 3H). 5-224 (B) δ 7.91 (bs, 1H),7.4-7.55 (m, 6H), 6.84 (s, 1H), 6.79 (s, 1H), 4.66 (d, J = 4.9 Hz, 2H),4.07 (d, J = 17.0 Hz, 1H), 3.80 (s, 3H), 3.77 (d, J = 17.0 Hz, 1H), 2.45(s, 3H). 5-225 (B) δ 7.25-7.55 (m, 7H), 6.9-7.0 (m, 1H), 6.84 (s, 1H),4.57 (d, J = 5.5 Hz, 2H), 4.07 (d, J = 17.0 Hz, 1H), 3.70 (d, J = 17.0Hz, 1H), 3.63 (s, 3H), 2.42 (s, 3H). 5-226 (B) δ 8.62 (s, 1H), 7.35-7.65(m, 6H), 6.8-6.9 (m, 1H), 5.07 (d, J = 6.1 Hz, 2H), 4.06 (d, J = 17.0Hz, 1H), 3.69 (d, J = 17.0 Hz, 1H), 2.42 (s, 3H). 5-227 (B) δ 7.45-7.55(m, 5H), 7.35-7.4 (m, 1H), 6.9-6.95 (m, 1H), 4.80 (d, J = 5.8 Hz, 2H),4.08 (d, J = 17.0 Hz, 1H), 3.71 (d, J = 17.0 Hz, 1H), 2.68 (s, 3H), 2.41(s, 3H). 5-230 (A) δ 8.43 (s, 1H), 7.45-7.55 (m, 5H), 7.43 (s, 1H), 6.68(t, J = 5.7 Hz, 1H), 4.90 (d, J = 5.7 Hz, 2H), 4.09 (d, J = 17.1 Hz,1H), 3.71 (d, J = 17.1 Hz, 1H), 2.48 (s, 3H). 5-231 (A) δ 7.45-7.55 (m,5H), 7.43 (s, 1H), 6.78 (t, J = 5.7 Hz, 1H), 4.80 (d, J = 5.7 Hz, 2H),4.09 (d, J = 17.1 Hz, 1H), 3.72 (d, J = 17.1 Hz, 1H), 2.54 (s, 3H), 2.47(s, 3H). 5-232 (A) δ 9.14 (s, 1H), 7.45-7.55 (m, 6H), 6.85 (t, J = 5.7Hz, 1H), 5.09 (d, J = 5.7 Hz, 2H), 4.08 (d, J = 17.4 Hz, 1H), 3.70 (d, J= 17.4 Hz, 1H), 2.48 (s, 3H). 5-233 (B) δ 8.42 (s, 1H), 8.05-8.15 (m,1H), 7.87 (s, 1H), 7.35-7.55 (m, 6H), 5.70 (d, J = 6.4 Hz, 2H), 4.08 (d,J = 17.0 Hz, 1H), 3.72 (d, J = 17.0 Hz, 1H), 2.32 (s, 3H). 5-235 (A) δ8.52 (d, J = 4.8 Hz, 1H), 7.65-7.75 (m, 1H), 7.15-7.55 (m, 9H), 5.32(dq, J = 6.9 Hz, 1H), 4.09 (d, J = 16.8 Hz, 1H), 3.70 (d, J = 16.8 Hz,1H), 2.48 (s, 3H), 1.59 (d, J = 6.9 Hz, 3H). 5-238 (B) δ 7.66 (t, J =7.7 Hz, 1H), 7.45-7.55 (m, 5H), 7.43 (t, J = 1.8 Hz, 1H), 7.25-7.35 (m,2H), 7.02 (t, J = 5.3 Hz, 1H), 4.69 (d, J = 5.3 Hz, 2H), 4.10 (d, J =17.2 Hz, 1H), 3.72 (d, J = 17.4 Hz, 1H), 2.47 (s, 3H). 5-239 (B) δ8.2-8.3 (m, 1H), 7.55-7.65 (m, 2H), 7.45-7.55 (m, 3H), 7.4-7.5 (m, 3H),7.25-7.4 (m, 2H), 4.79 (d, J = 6.2 Hz, 2H), 4.07 (d, J = 17.2 Hz, 1H),3.69 (d, J = 17.2 Hz, 1H), 2.41 (s, 3H). 5-240 (A) δ 8.58 (d, J = 1.8Hz, 1H), 8.53 (dd, J = 4.8, 1.8 Hz, 1H), 7.72 (d, J = 7.8 Hz, 1H),7.4-7.55 (m, 6H), 7.30 (dd, J = 7.8, 4.8 Hz, 1H), 6.40 (t, J = 6.0 Hz,1H), 4.63 (d, J = 6.0 Hz, 2H), 4.08 (d, J = 17.4 Hz, 1H), 3.70 (d, J =17.4 Hz, 1H), 2.46 (s, 3H). 5-242 (A) δ 8.57 (d, J = 6.0 Hz, 2H),7.4-7.55 (m, 6H), 7.26 (d, J = 6.0 Hz, 2H), 6.42 (t, J = 6.0 Hz, 1H),4.64 (d, J = 6.0 Hz, 2H), 4.08 (d, J = 17.4 Hz, 1H), 3.70 (d, J = 17.4Hz, 1H), 2.48 (s, 3H). 5-243 (A) δ 8.73 (d, J = 5.4 Hz, 2H), 7.5-7.6 (m,5H), 7.43 (s, 1H), 7.24 (t, J = 5.4 Hz, 1H), 7.19 (bs, 1H), 4.89 (d, J =5.2 Hz, 2H), 4.10 (d, J = 17.0 Hz, 1H), 3.72 (d, J = 17.0 Hz, 1H), 2.53(s, 3H). 5-245 (A) δ 9.18 (bs, 1H), 8.73 (d, J = 5.2 Hz, 1H), 7.56 (s,3H), 7.52 (bs, 2H), 7.4-7.45 (m, 1H), 7.35-7.4 (m, 1H), 7.04 (bs, 1H),4.77 (d, J = 4.8 Hz, 2H), 4.10 (d, J = 17.2 Hz, 1H), 3.72 (d, J = 17.2Hz, 1H), 2.52 (s, 3H). 5-246 (B) δ 8.69 (s, 1H), 8.53 (s, 2H), 7.5-7.55(m, 5H), 7.4-7.45 (m, 1H), 6.95-7.0 (m, 1H), 4.81 (d, J = 5.3 Hz, 2H),4.09 (d, J = 17.0 Hz, 1H), 3.71 (d, J = 17.0 Hz, 1H), 2.49 (s, 3H).5-247 (B) δ 8.55-8.6 (m, 1H), 8.35-8.4 (m, 1H), 7.4-7.55 (m, 6H),6.95-7.05 (m, 1H), 4.75-4.8 (m, 2H), 4.08 (d, J = 17.0 Hz, 1H), 3.72 (d,J = 17.0 Hz, 1H), 2.57 (s, 3H), 2.46 (s, 3H). 5-265 (B) δ 7.5-7.55 (m,5H), 7.4-7.45 (m, 1H), 6.70 (bs, 1H), 4.08 (d, J = 19.0 Hz, 1H), 3.70(d, J = 19.0 Hz, 1H), 2.51 (s, 3H), 1.51 (s, 9H). 5-277 (C) δ 7.45-7.65(m, 6H), 7.44 (s, 1H), 7.33 (d, J = 7.8 Hz, 1H), 7.21 (t, J = 7.8 Hz,1H), 7.00 (d, J = 7.8 Hz, 1H), 6.89 (t, J = 7.8 Hz, 1H), 6.69 (s, 1H),4.08 (d, J = 17.4 Hz, 1H), 3.61 (d, J = 17.4 Hz, 1H), 2.53 (s, 3H).5-278 (C) δ 7.45-7.65 (m, 6H), 7.44 (s, 1H), 7.20 (t, J = 8.4 Hz, 1H),6.85-6.95 (m, 2H), 6.81 (d, J = 8.4 Hz, 1H), 6.33 (s, 1H), 4.10 (d, J =17.1 Hz, 1H), 3.71 (d, J = 17.1 Hz, 1H), 2.52 (s, 3H). 5-279 (A) δ 7.95(s, 1H), 7.35-7.55 (m, 6H), 7.17 (d, J = 8.4 Hz, 2H), 6.79 (d, J = 8.4Hz, 2H), 6.42 (bs, 1H), 4.09 (d, J = 17.4 Hz, 1H), 3.71 (d, J = 17.4 Hz,1H), 2.43 (s, 3H). 5-280 (A) δ 7.4-7.65 (m, 10H), 6.98 (d, J = 8.4 Hz,2H), 4.10 (d, J = 17.3 Hz, 1H), 3.72 (d, J = 17.3 Hz, 1H), 2.52 (s, 3H).5-296 (A) δ 8.76 (bs, 1H), 8.12 (bs, 1H), 8.02 (d, J = 5.4 Hz, 1H),7.35-7.5 (m, 6H), 6.26 (d, J = 5.4 Hz, 1H), 4.10 (d, J = 17.4 Hz, 1H),3.73 (d, J = 17.4 Hz, 1H), 2.45 (s, 3H), 2.43 (s, 3H). 5-299 (C) δ 10.15(bs, 1H), 9.37 (bs, 1H), 8.40 (s, 1H), 7.5-7.6 (m, 5H), 7.46 (s, 1H),6.69 (s, 1H), 4.17 (d, J = 17.4 Hz, 1H), 3.86 (d, J = 17.4 Hz, 1H), 2.59(s, 3H). 5-301 (A) δ 7.4-7.65 (m, 7H), 7.34 (d, J = 9.3 Hz, 1H), 7.01(d, J = 9.3 Hz, 1H), 4.10 (d, J = 17.4 Hz, 1H), 4.13 (d, J = 17.4 Hz,1H), 3.71 (d, J = 17.4 Hz, 1H), 2.52 (s, 3H). 5-303 (B) δ 10.38 (bs,1H), 7.2-8.65 (m, 11H), 4.05-4.2 (m, 1H), 3.7-3.85 (m, 1H), 2.44 and2.37 (s, 3H). 5-311 (A) δ 7.3-7.75 (m, 6H), 6.52 (t, J = 6.3 Hz, 1H),4.05-4.2 (m, 3H), 3.77 (d, J = 17.4 Hz, 1H), 2.60 (s, 3H). 5-312 (A) δ7.25-7.65 (m, 6H), 6.54 (t, J = 6.3 Hz, 1H), 3.9-4.15 (m, 2H), 4.10 (d,J = 17.7 Hz, 1H), 3.73 (d, J = 17.7 Hz, 1H), 2.74 (q, J = 7.2 Hz, 2H),1.19 (t, J = 7.2 Hz, 3H). 5-313 (A) δ 8.50 (d, J = 4.8 Hz, 1H), 7.70 (t,J = 4.5 Hz, 1H), 7.5-7.6 (m, 3H), 7.49 (bs, 2H), 7.42 (bs, 1H),7.15-7.35 (m, 3H), 4.73 (d, J = 4.5 Hz, 2H), 4.11 (d, J = 17.4 Hz, 1H),3.73 (d, J = 17.4 Hz, 1H), 2.84 (q, J = 7.5 Hz, 2H), 1.23 (t, J = 7.5Hz, 3H). 5-316 (B) δ 7.72 (bs, 3H), 7.51 (bs, 2H), 7.45 (t, J = 1.8 Hz,1H), 7.15-7.25 (m, 1H), 4.71 (d, J = 6.0 Hz, 2H), 4.15-4.2 (m, 3H), 3.73(d, J = 17.2 Hz, 1H), 3.34 (t, J = 6.0 Hz, 1H). 5-318 (A) δ 8.30 (d, J =8.4 Hz, 1H), 8.18 (bs, 1H), 7.51 (s, 2H), 7.48 (s, 1H), 7.25-7.45 (m,6H), 7.16 (d, J = 8.4 Hz, 1H), 4.68 (d, J = 5.7 Hz, 2H), 4.11 (d, J =17.4 Hz, 1H), 3.97 (s, 3H), 3.73 (d, J = 17.4 Hz, 1H). 5-320 (B) δ 8.11(d, J = 8.0 Hz, 1H), 7.70 (s, 1H), 7.64 (d, J = 8.0 Hz, 1H), 7.51 (s,2H), 7.45 (s, 1H), 6.86 (t, J = 6.0 Hz, 1H), 4.0-4.25 (m, 3H), 3.71 (d,J = 17.6, 1H). 5-322 (A) δ 8.14 (t, J = 7.8 Hz, 1H), 7.54 (d, J = 7.8Hz, 1H), 7.50 (d, J = 7.8 Hz, 1H), 7.34 (s, 1H), 7.31 (s, 1H), 7.23 (s,1H), 7.09 and 7.05 (t, J = 6.3 Hz, 1H), 4.18 (qd, J = 18.5, 6.3 Hz, 2H),4.08 (d, J = 17.4 Hz, 1H), 3.74 (d, J = 17.4 Hz, 1H), 2.52 (s, 3H).5-325 (A) δ 8.59 (bs, 1H), 8.32 (s, 1H), 8.11 (bs, 1H), 8.03 (d, J = 8.1Hz, 1H), 7.85 (d, J = 8.1 Hz, 1H), 7.73 (t, J = 8.1 Hz, 1H), 7.51 (bs,2H), 7.43 (bs, 1H), 7.2-7.4 (m, 2H), 4.73 (bs, 2H), 4.23 and 4.21 (d, J= 17.4 Hz, 1H), 3.86 and 3.85 (d, J = 17.4 Hz, 1H), 2.96 and 2.93 (s,3H). 5-328 (A) δ 8.16 (t, J = 8.0 Hz, 1H), 7.6-7.8 (m, 3H), 7.56 (d, J =8.0 Hz, 1H), 7.52 (d, J = 8.1 Hz, 1H), 7.08 and 7.03 (t, J = 6.5 Hz,1H), 4.35-4.55 (m, 2H), 4.05-4.25 (m, 2H), 4.14 (d, J = 17.4 Hz, 1H),3.79 (d, J = 17.4 Hz, 1H). 5-330 (B) δ 8.57 (d, J = 4.8 Hz, 1H), 7.71(td, J = 7.7, 1.8 Hz, 1H), 7.62 (t, J = 4.6 Hz, 1H), 7.54 (d, J = 8.6Hz, 1H), 7.50 (d, J = 1.6 Hz, 2H), 7.42 (t, J = 1.8 Hz, 1H), 7.33 (d, J= 7.9 Hz, 1H), 7.24 (dd, J = 7.5, 5.0 Hz, 1H), 6.9-7.0 (m, 2H), 5.73(bs, 2H), 4.72 (d, J = 4.8 Hz, 2H), 4.04 (d, J = 17.2 Hz, 1H), 3.66 (d,J = 17.4 Hz, 1H). 5-332 (A) δ 8.57 (d, J = 4.2 Hz, 1H), 7.65-7.75 (m,2H), 7.45-7.6 (m, 4H), 7.43 (bs, 1H), 7.33 (d, J = 7.8 Hz, 1H), 7.2-7.3(m, 1H), 6.93 (bs, 1H), 6.85 (d, J = 7.8 Hz, 1H), 4.71 (d, J = 4.8 Hz,2H), 4.09 (d, J = 17.1 Hz, 1H), 3.69 (d, J = 17.1 Hz, 1H), 2.90 (d, J =3.6 Hz, 3H). 5-335 (A) δ 10.29 (bs, 1H), 8.56 (d, J = 6.0 Hz, 1H), 8.18(d, J = 8.1 Hz, 1H), 7.15-7.75 (m, 8H), 4.79 (d, J = 5.4 Hz, 2H), 4.10(d, J = 17.1 Hz, 1H), 3.71 (d, J = 17.1 Hz, 1H), 2.75 (s, 6H). 5-336 (A)δ 8.45-8.6 (m, 1H), 8.23 and 8.29 (s, 1H), 7.15-7.9 (m, 10H), 4.65-4.75(m, 2H), 4.0-4.2 (m, 1H), 3.6-3.8 (m, 1H), 3.25 and 3.34 (s, 3H). 5-337(A) δ 8.45-8.6 (m, 1H), 7.15-8.05 (m, 10H), 4.65-4.75 (m, 2H), 4.0-4.2(m, 1H), 3.65-3.8 (m, 1H), 3.33 and 3.22 (s, 3H), 2.19 and 1.87 (s, 3H).5-340 (B) δ 7.95-8.0 (m, 1H), 7.89 (dd, J = 8.0, 2.6 Hz, 1H), 7.79 (dd,J = 7.8, 1.6 Hz, 1H), 7.52 (bs, 2H), 7.44 (t, J = 1.8 Hz, 1H), 5.51 (s,1H), 4.45-4.55 (m, 1H), 4.14 (dd, J = 20.2, 7.6 Hz, 1H), 3.9-4.05 (m,1H), 3.77 (dd, J = 17.4, 5.2 Hz, 1H). 5-342 (B) δ 7.9-7.95 (bs, 2H),7.53 (d, J = 1.8 Hz, 1H), 7.44 (dd, J = 8.2, 1.8 Hz, 1H), 7.21 (bs, 2H),7.14 (t, J = 1.8 Hz, 1H), 3.75-3.9 (m, 3H), 0.30 (s, 9H). 5-343 (B) δ7.25-7.8 (m, 11H), 5.65 (t, J = 6.0 Hz, 1H), 4.10 (d, J = 17.2 Hz, 1H),3.7-3.85 (m, 3H). 5-345 (A) δ 8.47 (s, 1H), 8.43 (d, J = 4.8 Hz, 1H),7.95 (s, 1H), 7.6-7.85 (m, 5H), 7.50 (bs, 2H), 7.43 (bs, 1H), 7.15-7.25(m, 2H), 4.55 (d, J = 5.4 Hz, 2H), 4.13 (d, J = 17.7 Hz, 1H), 3.77 (d, J= 17.7 Hz, 1H). 5-346 (B) δ 7.91 (ddd, J = 8.6, 6.8, 1.8 Hz, 1H), 7.78(ddd, J = 8.6, 6.8, 1.8 Hz, 1H), 7.49 (d, J = 1.6 Hz, 2H), 7.45 (t, J =2.0 Hz, 1H), 6.84 (bs, 1H), 4.15-4.25 (m, 3H), 3.80 (bs, 1H). 5-347 (B)δ 7.85-7.95 (m, 1H), 7.7-7.8 (m, 1H), 7.25-7.5 (m, 8H), 6.90 (bs, 1H),4.68 (d, J = 5.4 Hz, 2H), 4.16 (bs, 1H), 3.78 (bs, 1H). 5-348 (B) δ 8.59(bs, 1H), 8.11 (bs, 1H), 7.89 (bs, 1H), 7.71 (bs, 2H), 7.2-7.5 (m, 5H),4.80 (bs, 2H), 4.18 (d, J = 17.8 Hz, 1H), 3.80 (d, J = 17.8 Hz, 1H).5-352 (A) δ 8.49 (d, J = 4.5 Hz, 1H), 7.65-7.75 (m, 1H), 7.51 (s, 2H),7.42 (s, 1H), 7.3-7.4 (m, 3H), 7.22 (dd, J = 7.5, 4.5 Hz, 1H), 7.10 (bs,1H), 4.76 (d, J = 4.5 Hz, 2H), 4.07 (d, J = 17.4 Hz, 1H), 3.69 (d, J =17.4 Hz, 1H), 2.33 (s, 6H). 5-353 (A) δ 8.77 (d, J = 2.4 Hz, 1H), 7.73(d, J = 8.1 Hz, 1H), 7.70 (s, 1H), 7.60 (d, J = 8.1 Hz, 1H), 7.52 (bs,2H), 7.43 (bs, 1H), 7.33 (d, J = 2.4 Hz, 1H), 7.10 (t, J = 5.4 Hz, 1H),4.81 (d, J = 5.4 Hz, 2H), 4.12 (d, J = 17.4 Hz, 1H), 3.72 (d, J = 17.4Hz, 1H). 5-354 (A) δ 8.53 (d, J = 4.5 Hz, 1H), 7.55-7.8 (m, 5H), 7.53(bs, 2H), 7.43 (bs, 1H), 7.2-7.4 (m, 2H), 4.77 (d, J = 4.8 Hz, 2H), 4.13(d, J = 17.4 Hz, 1H), 3.74 (d, J = 17.4 Hz, 1H). 5-356 (A) δ 7.4-7.6 (m,6H), 6.17 (bs, 1H), 4.12 (d, J = 17.6 Hz, 1H), 3.72 (d, J = 17.6 Hz,1H), 3.55-3.7 (m, 4H), 3.53 (q, J = 7.1 Hz, 2H), 2.47 (s, 3H), 1.20 (t,J = 7.1 Hz, 3H). 5-357 (A) δ 7.4-7.6 (m, 6H), 5.97 (t, J = 5.6 Hz, 1H),4.50 (t, J = 5.6 Hz, 1H), 4.12 (d, J = 17.6 Hz, 1H), 3.72 (d, J = 17.6Hz, 1H), 3.60 (t, J = 5.6 Hz, 2H), 3.43 (s, 6H), 2.48 (s, 3H). 5-358 (A)δ 7.4-7.6 (m, 6H), 5.75-6.0 (m, 2H), 5.27 (d, J = 17.1 Hz, 1H), 5.21 (d,J = 10.2 Hz, 1H), 4.0-4.2 (m, 3H), 3.72 (d, J = 17.3 Hz, 1H), 2.48 (s,3H). 5-359 (A) δ 8.79 (d, J = 2.1 Hz, 1H), 7.3-7.6 (m, 7H), 6.54 (t, J =5.4 Hz, 1H), 4.77 (d, J = 5.4 Hz, 2H), 4.12 (d, J = 17.6 Hz, 1H), 3.72(d, J = 17.6 Hz, 1H), 2.47 (s, 3H). 5-360 (A) δ 8.54 (d, J = 5.0 Hz,1H), 7.65-7.8 (m, 1H), 7.15-7.6 (m, 9H), 4.74 (d, J = 5.0 Hz, 2H), 4.08(d, J = 17.6 Hz, 1H), 3.72 (d, J = 17.6 Hz, 1H), 2.50 (s, 3H). 5-361 (B)δ 7.5-7.55 (m, 4H), 7.43 (d, J = 5.0 Hz, 1H), 7.42 (d, J = 1.8 Hz, 1H),6.07 (t, J = 6.4 Hz, 1H), 4.27 (d, J = 17.4 Hz, 1H), 4.05-4.15 (m, 2H),3.68 (dd, J = 17.4, 1.8 Hz, 1H), 2.46 (s, 3H). 5-362 (B) δ 8.5-8.55 (m,1H), 7.71 (td, J = 7.6, 1.6 Hz, 1H), 7.5-7.55 (m, 4H), 7.42 (t, J = 1.6Hz, 1H), 7.34 (d, J = 7.8 Hz, 1H), 7.2-7.3 (m, 3H), 4.75 (d, J = 4.8 Hz,2H), 4.27 (d, J = 17.2 Hz, 1H), 3.68 (d, J = 17.2 Hz, 1H), 2.50 (s, 3H).5-364 (A) δ 7.3-7.6 (m, 6H), 6.07 (t, J = 6.3 Hz, 1H), 3.8-4.25 (m, 7H),3.41 (d, J = 16.8 Hz, 1H), 2.46 (s, 3H). 5-365 (A) δ 8.52 (d, J = 3.8Hz, 1H), 7.65-7.75 (m, 1H), 7.15-7.6 (m, 9H), 4.75 (d, J = 4.6 Hz, 2H),3.8-4.2 (m, 5H), 3.41 (d, J = 16.8 Hz, 1H), 2.50 (s, 3H). 5-366 (A) δ7.3-7.55 (m, 6H), 6.83 (t, J = 6.5 Hz, 1H), 4.20 (d, J = 17.4 Hz, 1H),4.0-4.15 (m, 2H), 3.62 (d, J = 17.4 Hz, 1H), 2.40 (s, 3H), 2.30 (s, 3H).5-368 (B) δ 7.5-7.6 (m, 2H), 7.4-7.5 (m, 4H), 6.0-6.5 (m, 1H), 4.1-4.2(m, 2H), 3.53 (d, J = 3.2 Hz, 2H), 2.50 (s, 3H), 1.64 (d, J = 3.2 Hz,2H), 0.04 (s, 9H). 5-369 (B) δ 8.55-8.6 (m, 1H), 7.7-7.8 (m, 1H),7.5-7.55 (m, 3H), 7.35-7.45 (m, 3H), 7.2-7.3 (m, 3H), 4.79 (d, J = 4.8Hz, 2H), 3.53 (d, J = 3.2 Hz, 2H), 2.55 (s, 3H), 1.64 (d, J = 5.8 Hz,2H), 0.04 (s, 9H). 5-370 (A) δ 7.47 (s, 1H), 7.45 (d, J = 7.8 Hz, 1H),7.34 (d, J = 7.8 Hz, 1H), 7.15-7.3 (m, 3H), 6.28 (t, J = 6.5 Hz, 1H),4.07 (qd, J = 18.5, 6.5 Hz, 2H), 3.61 (d, J = 16.2 Hz, 1H), 3.53 (d, J =16.2 Hz, 1H), 2.40 (s, 3H), 0.11 (s, 9H). 5-371 (A) δ 8.50 (d, J = 5.1Hz, 1H), 7.45-7.75 (m, 4H), 7.15-7.35 (m, 6H), 4.72 (d, J = 5.1 Hz, 2H),3.63 (d, J = 16.2 Hz, 1H), 3.54 (d, J = 16.2 Hz, 1H), 2.48 (s, 3H), 0.11(s, 9H). 5-372 (A) δ 8.60 (d, J = 4.7 Hz, 1H), 7.15-7.75 (m, 9H), 6.05(t, J = 6.0 Hz, 1H), 4.77 (d, J = 16.8 Hz, 1H), 4.0-4.2 (m, 2H), 3.69(d, J = 16.8 Hz, 1H), 2.45 (s, 3H). 5-373 (A) δ 8.60 (d, J = 4.9 Hz,1H), 8.53 (d, J = 5.1 Hz, 1H), 7.15-7.8 (m, 13H), 4.7-4.85 (m, 3H), 3.69(d, J = 16.7 Hz, 1H), 2.48 (s, 3H). 5-374 (A) δ 7.3-7.75 (m, 6H),6.0-6.5 (br, 1H), 3.95-4.25 (m, 3H), 3.70 (d, J = 17.1 Hz, 1H), 2.42 (s,3H). 5-375 (A) δ 8.55 (d, J = 4.8 Hz, 1H), 7.45-7.75 (m, 7H), 7.3-7.45(m, 2H), 7.15-7.3 (m, 1H), 4.74 (d, J = 5.1 Hz, 2H), 4.09 (d, J = 17.4Hz, 1H), 3.70 (d, J = 17.4 Hz, 1H), 2.49 (s, 3H). 5-377 (A) δ 8.53 (d, J= 4.5 Hz, 1H), 7.55-7.8 (m, 8H), 7.15-7.4 (m, 2H), 4.77 (d, J = 4.5 Hz,2H), 4.08 (d, J = 17.4 Hz, 1H), 3.71 (d, J = 17.4 Hz, 1H). 5-378 (A) δ7.65-7.8 (m, 3H), 7.4-7.6 (m, 3H), 6.04 (t, J = 6.3 Hz, 1H), 4.0-4.2 (m,3H), 3.70 (d, J = 17.0 Hz, 1H), 2.47 (s, 3H). 5-379 (A) δ 7.73 (bs, 1H),7.71 (bs, 2H), 7.51 (s, 1H), 7.49 (d, J = 8.7 Hz, 1H), 7.42 (d, J = 8.7Hz, 1H), 6.2-6.3 (m, 1H), 4.08 (d, J = 17.4 Hz, 1H), 3.71 (d, J = 17.4Hz, 1H), 3.5-3.65 (m, 4H), 3.38 (s, 3H), 2.45 (s, 3H). 5-380 (A) δ 7.74(bs, 1H), 7.71 (bs, 2H), 7.51 (s, 1H), 7.50 (d, J = 8.4 Hz, 1H), 7.42(d, J = 8.4 Hz, 1H), 6.2-6.3 (m, 1H), 4.08 (d, J = 17.4 Hz, 1H), 3.71(d, J = 17.4 Hz, 1H), 3.55-3.65 (m, 4H), 3.53 (q, J = 7.2 Hz, 2H), 2.46(s, 3H), 1.20 (t, J = 7.2 Hz, 3H). 5-381 (A) δ 7.73 (bs, 1H), 7.70 (bs,2H), 7.51 (s, 1H), 7.50 (d, J = 8.4 Hz, 1H), 7.41 (d, J = 8.4 Hz, 1H),6.06 (t, J = 5.4 Hz, 1H), 4.50 (t, J = 5.4 Hz, 1H), 4.08 (d, J = 16.8Hz, 1H), 3.70 (d, J = 16.8 Hz, 1H), 3.59 (t, J = 5.4 Hz, 2H), 3.43 (s,6H), 2.46 (s, 3H). 5-382 (A) δ 7.73 (bs, 1H), 7.71 (bs, 2H), 7.50 (s,1H), 7.49 (d, J = 8.7 Hz, 1H), 7.45 (d, J = 8.7 Hz, 1H), 6.47 (t, J =5.4 Hz, 1H), 4.20 (d, J = 5.4 Hz, 2H), 4.09 (d, J = 17.4 Hz, 1H), 3.80(s, 3H), 3.72 (d, J = 17.4 Hz, 1H), 2.46 (s, 3H). 5-385 (A) δ 7.74 (bs,1H), 7.70 (bs, 2H), 7.49 (s, 1H), 7.48 (d, J = 8.7 Hz, 1H), 7.39 (d, J =8.7 Hz, 1H), 6.06 (t, J = 5.4 Hz, 1H), 5.92 (ddd, J = 15.9, 10.2, 5.4Hz, 1H), 5.26 (d, J = 15.9 Hz, 1H), 5.19 (d, J = 10.2 Hz, 1H), 4.08 (d,J = 17.4 Hz, 1H), 4.05 (t, J = 5.4 Hz, 2H), 3.71 (d, J = 17.4 Hz, 1H),2.45 (s, 3H). 5-386 (A) δ 8.76 (d, J = 2.1 Hz, 1H), 7.73 (bs, 1H), 7.70(bs, 2H), 7.49 (s, 1H), 7.48 (d, J = 8.1 Hz, 1H), 7.42 (d, J = 8.1 Hz,1H), 7.29 (d, J = 2.1 Hz, 1H), 6.75 (t, J = 5.4 Hz, 1H), 4.76 (d, J =5.4 Hz, 2H), 4.08 (d, J = 17.4 Hz, 1H), 3.70 (d, J = 17.4 Hz, 1H), 2.44(s, 3H). 5-387 (A) δ 8.53 (d, J = 5.1 Hz, 1H), 7.65-7.8 (m, 4H), 7.53(s, 3H), 7.33 (d, J = 8.1 Hz, 1H), 7.15-7.3 (m, 2H), 4.75 (d, J = 4.8Hz, 2H), 4.08 (d, J = 17.1 Hz, 1H), 3.70 (d, J = 17.1 Hz, 1H), 2.51 (s,3H). 5-388 (A) δ 8.5-8.55 (m, 1H), 7.65-7.75 (m, 1H), 7.5-7.6 (m, 3H),7.2-7.45 (m, 6H), 4.75 (d, J = 4.8 Hz, 2H), 4.07 (d, J = 17.2 Hz, 1H),3.72 (d, J = 17.2 Hz, 1H), 2.51 (s, 3H), 2.39 (s, 3H). 5-389 (A) δ 8.09(s, 2H), 7.98 (s, 1H), 7.45-7.55 (m, 2H), 7.38 (d, J = 8.4 Hz, 1H), 6.35(bs, 1H), 4.21 (d, J = 17.4 Hz, 1H), 4.0-4.15 (m, 2H), 3.77 (d, J = 17.4Hz, 1H), 2.42 (s, 3H). 5-390 (A) δ 8.53 (d, J = 4.2 Hz, 1H), 8.10 (s,2H), 7.97 (s, 1H), 7.65-7.8 (m, 1H), 7.54 (bs, 3H), 7.2-7.35 (m, 3H),4.75 (d, J = 4.5 Hz, 2H), 4.22 (d, J = 17.1 Hz, 1H), 3.77 (d, J = 17.1Hz, 1H), 2.50 (s, 3H). 5-391 (A) δ 8.52 (d, J = 5.1 Hz, 1H), 7.72 (t, J= 4.8 Hz, 1H), 7.52 (bs, 3H), 7.15-7.35 (m, 4H), 7.07 (d, J = 9.3 Hz,1H), 6.96 (d, J = 9.3 Hz, 1H), 4.73 (d, J = 4.8 Hz, 2H), 4.10 (d, J =17.4 Hz, 1H), 3.72 (d, J = 17.4 Hz, 1H), 2.51 (s, 3H), 2.50 (s, 3H).5-392 (A) δ 8.53 (d, J = 4.8 Hz, 1H), 7.6-7.75 (m, 4H), 7.3-7.4 (m, 4H),7.15-7.35 (m, 2H), 4.77 (d, J = 5.1 Hz, 2H), 4.08 (d, J = 17.1 Hz, 1H),3.72 (d, J = 17.1 Hz, 1H), 2.52 (s, 3H), 2.50 (s, 3H). 5-393 (A) δ 8.52(d, J = 4.5 Hz, 1H), 7.70 (t, J = 4.8 Hz, 1H), 7.53 (bs, 1H), 7.52 (bs,2H), 7.15-7.45 (m, 6H), 4.74 (d, J = 4.8 Hz, 2H), 4.12 (d, J = 17.4 Hz,1H), 3.89 (s, 3H), 3.75 (d, J = 17.4 Hz, 1H), 2.50 (s, 3H). 5-394 (A) δ8.52 (d, J = 5.1 Hz, 1H), 7.70 (t, J = 4.8 Hz, 1H), 7.52 (bs, 3H),7.15-7.35 (m, 5H), 7.13 (bs, 1H), 4.74 (d, J = 4.8 Hz, 2H), 4.07 (d, J =17.4 Hz, 1H), 3.73 (d, J = 17.4 Hz, 1H), 2.51 (s, 6H), 2.50 (s, 3H).5-398 (A) δ 8.56 (d, J = 4.5 Hz, 1H), 7.72 (td, J = 7.5, 1.5 Hz, 1H),7.65 (s, 2H), 7.45-7.6 (m, 4H), 7.39 (d, J = 7.8 Hz, 1H), 7.15-7.3 (m,1H), 4.72 (d, J = 5.1 Hz, 2H), 4.10 (d, J = 17.4 Hz, 1H), 3.71 (d, J =17.4 Hz, 1H), 2.46 (s, 3H). 5-399 (B) δ 7.35-7.55 (m, 6H), 6.12 (bs,1H), 4.18 (d, J = 17.2 Hz, 1H), 3.65-3.75 (m, 3H), 2.4-2.55 (m, 5H).5-400 (B) δ 7.4-7.6 (m, 6H), 6.87 (d, J = 9.2 Hz, 1H), 5.9-6.0 (m, 1H),4.08 (dd, J = 17.2 Hz, 1H), 3.71 (d, J = 17.2 Hz, 1H), 2.48 (s, 3H).5-401 (B) δ 7.4-7.6 (m, 6H), 6.27 (d, J = 10.4 Hz, 1H), 5.6-5.8 (m, 1H),4.08 (d, J = 17.6 Hz, 1H), 3.71 (d, J = 17.6 Hz, 1H), 3.61 (s, 3H), 2.50(s, 3H). 5-403 (A) δ 7.35-7.7 (m, 6H), 6.8 (s, 1H), 4.09 (d, J = 17.4Hz, 1H), 3.73 (d, J = 17.4 Hz, 1H), 3.55 (q, J = 5.4 Hz, 2H), 2.74 (t, J= 5.7 Hz, 2H), 2.60 (bs, 4H), 2.45 (s, 3H), 1.79 (bs, 4H). 5-404 (A) δ7.35-7.6 (m, 6H), 6.77 (s, 1H), 4.10 (d, J = 17.4 Hz, 1H), 3.73 (d, J =17.4 Hz, 1H), 3.53 (q, J = 5.7 Hz, 2H), 2.57 (t, J = 6.0 Hz, 2H), 2.47(bs, 7H), 1.55-1.65 (m, 4H), 1.35-1.5 (m, 2H). 5-405 (B) δ 7.45-7.55 (m,5H), 7.43 (t, J = 1.8 Hz, 1H), 6.56 (d, J = 5.7 Hz, 1H), 4.58 (ddd, J =10.6, 8.4, 5.7 Hz, 1H), 4.09 (d, J = 17.2 Hz, 1H), 3.95-4.05 (m, 1H),3.8-3.9 (m, 1H), 3.71 (d, J = 17.2 Hz, 1H), 3.5-3.65 (m, 2H), 2.85-2.9(m, 1H), 2.48 (s, 3H), 2.0-2.15 (m, 1H). 5-406 (B) δ 7.4-7.55 (m, 6H),6.52 (t, J = 6.0 Hz, 1H), 5.35 (bs, 1H), 4.8-4.95 (m, 1H), 4.09 (d, J =17.4 Hz, 1H), 3.6-3.95 (m, 3H), 3.75 (d, J = 17.4 Hz, 1H), 3.4-3.5 (m,1H), 2.45 (s, 3H). 5-407 (B) δ 7.5-7.55 (m, 5H), 7.43 (t, J = 1.8 Hz,1H), 6.84 (d, J = 7.0 Hz, 1H), 5.37 (d, J = 7.1 Hz, 1H), 4.09 (d, J =17.2 Hz, 1H), 3.87 (s, 6H), 3.72 (d, J = 17.2 Hz, 1H), 2.49 (s, 3H).5-409 (A) δ 9.80 and 8.65 (bs, 1H), 7.4-7.6 (m, 6H), 7.1 and 6.64 (bs,1H), 5.94 (bs, 1H), 5.2-5.5 (m, 2H), 3.95-4.45 (m, 5H), 3.73 (d, J =17.0 Hz, 1H), 2.42 (s, 3H). 5-410 (B) δ 7.4-7.55 (m, 6H), 6.72 (bs, 1H),6.37 (bs, 1H), 4.65 (q, J = 7.4 Hz, 1H), 4.08 (d, J = 17.4 Hz, 1H), 3.70(d, J = 17.4 Hz, 1H), 3.25-3.35 (m, 2H), 2.45 (s, 3H), 1.47 (d, J = 7.4Hz, 3H), 1.16 (t, J = 7.4 Hz, 3H). 5-414 (B) δ 8.19 (t, J = 6.0 Hz, 1H),7.45-7.55 (m, 5H), 7.43 (t, J = 1.8 Hz, 1H), 7.21 (d, J = 7.5 Hz, 1H),4.93 (ddd, J = 11.9, 7.5, 4.2 Hz, 1H), 4.31 (bs, 1H), 4.09 (d, J = 17.2Hz, 1H), 4.0-4.1 (m, 1H), 3.65-3.9 (m, 3H), 3.72 (d, J = 17.2 Hz, 1H),2.47 (s, 3H), 2.15-2.25 (m, 1H), 1.8-1.9 (m, 1H). 5-415 (B) δ 7.67 (t, J= 6.6 Hz, 1H), 7.3-7.55 (m, 6H), 7.11 (d, J = 8.1 Hz, 1H), 4.9-5.0 (m,1H), 4.3-4.45 (m, 2H), 4.09 (d, J = 17.2 Hz, 1H), 3.8-3.9 (m, 2H), 3.73(d, J = 17.2 Hz, 1H), 3.03 (s, 3H), 2.33 (s, 3H), 2.2-2.4 (m, 2H). 5-417(B) δ 7.3-7.6 (m, 11H), 6.32 (d, J = 9.6 Hz, 1H), 6.24 (d, J = 9.6 Hz,1H), 4.07 (d, J = 17.2 Hz, 1H), 3.69 (d, J = 17.2 Hz, 1H), 3.59 (s, 3H),2.51 (s, 3H). 5-420 (A) δ 8.77 (bs, 1H), 7.35-7.55 (m, 6H), 6.81 (s,1H), 6.37 (d, J = 9.3 Hz, 1H), 6.31 (s, 1H), 6.15-6.25 (m, 1H), 5.9-6.05(m, 1H), 4.07 (d, J = 17.3 Hz, 1H), 3.69 (d, J = 17.3 Hz, 1H), 2.43 (s,3H). 5-421 (A) δ 8.69 (d, J = 4.8 Hz, 1H), 7.51 (s, 5H), 7.43 (s, 1H),7.25 (d, J = 4.8 Hz, 1H), 6.86 (t, J = 5.7 Hz, 1H), 4.82 (d, J = 5.7 Hz,2H), 4.09 (d, J = 17.1 Hz, 1H), 3.70 (d, J = 17.1 Hz, 1H), 2.50 (s, 3H).5-423 (B) δ 7.72 (d, J = 3.3 Hz, 1H), 7.45-7.55 (m, 5H), 7.43 (t, J =1.8 Hz, 1H), 7.31 (d, J = 3.3 Hz, 1H), 6.78 (d, J = 7.7 Hz, 1H),5.55-5.65 (m, 1H), 4.08 (d, J = 17.2 Hz, 1H), 3.71 (d, J = 17.2 Hz, 1H),2.47 (s, 3H), 1.72 (d, J = 6.8 Hz, 3H). 5-424 (A) δ 8.29 (d, J = 9.6 Hz,1H), 7.4-7.6 (m, 7H), 7.12 (s, 1H), 7.01 (s, 1H), 6.7-6.85 (m, 1H), 4.08(d, J = 17.3 Hz, 1H), 3.70 (d, J = 17.3 Hz, 1H), 2.38 (s, 3H). 5-425 (B)δ 7.45-7.55 (m, 6H), 7.34 (bs, 1H), 6.89 (bs, 1H), 6.58 (t, J = 4.8 Hz,1H), 4.52 (d, J = 15.8 Hz, 2H), 4.07 (d, J = 17.2 Hz, 1H), 3.69 (d, J =17.2 Hz, 1H), 3.67 (s, 3H), 2.46 (s, 3H). 5-426 (B) δ 8.33 (s, 1H), 7.92(s, 1H), 7.45-7.55 (m, 4H), 7.42 (t, J = 1.8 Hz, 1H), 7.25-7.35 (m, 2H),6.45-6.55 (m, 1H), 4.07 (d, J = 17.2 Hz, 1H), 3.71 (d, J = 17.2 Hz, 1H),2.29 (s, 3H), 1.87 (d, J = 6.6 Hz, 3H). 5-427 (A) δ 8.40 (s, 1H), 8.07(s, 1H), 7.2-7.6 (m, 7H), 6.9-7.1 (m, 1H), 4.08 (d, J = 16.5 Hz, 1H),3.70 (d, J = 16.5 Hz, 1H), 2.44 (s, 3H). 5-428 (A) δ 7.97 (s, 1H),7.4-7.65 (m, 6H), 4.54 (q, J = 8.3 Hz, 1H), 4.08 (d, J = 17.3 Hz, 1H),3.70 (d, J = 17.3 Hz, 1H), 2.49 (s, 3H). 5-434 (A) δ 7.4-7.85 (m, 11H),4.09 (d, J = 17.2 Hz, 1H), 3.72 (d, J = 17.2 Hz, 1H), 2.53 (s, 3H).5-450 (A) δ 8.52 (d, J = 4.5 Hz, 1H), 7.69 (t, J = 7.8 Hz, 1H), 7.4-7.6(m, 5H), 7.15-7.35 (m, 4H), 4.73 (d, J = 4.8 Hz, 2H), 4.49 (s, 1H), 3.99(d, J = 16.8 Hz, 1H), 3.65-3.85 (m, 3H), 3.3-3.65 (m, 1H), 3.33 (d, J =16.8 Hz, 1H), 2.48 (s, 3H), 1.20 (t, J = 6.9 Hz, 3H), 1.16 (t, J = 6.9Hz, 3H). 5-452 (A) δ 8.68 (s, 1H), 8.59 (s, 1H), 8.25 (s, 1H), 7.4-7.6(m, 3H), 6.06 (t, J = 6.2 Hz, 1H), 4.24 (d, J = 17.1 Hz, 1H), 4.0-4.2(m, 2H), 3.79 (d, J = 17.1 Hz, 1H), 2.47 (s, 3H). 5-453 (A) δ 8.69 (s,1H), 8.58 (s, 1H), 8.55 (d, J = 4.9 Hz, 1H), 8.26 (s, 1H), 7.71 (td, J =7.5, 1.5 Hz, 1H), 7.2-7.55 (m, 6H), 4.74 (d, J = 4.9 Hz, 2H), 4.25 (d, J= 17.3 Hz, 1H), 3.79 (d, J = 17.3 Hz, 1H), 2.50 (s, 3H). 5-455 (B) δ8.54 (ddd, J = 4.9, 1.6, 0.9 Hz, 1H), 7.70 (td, J = 7.7, 1.8 Hz, 1H),7.5-7.55 (m, 3H), 7.43 (s, 2H), 7.33 (d, J = 7.7 Hz, 1H), 7.2-7.3 (m,2H), 4.74 (d, J = 4.9 Hz, 2H), 4.63 (bs, 2H), 4.02 (d, J = 17.2 Hz, 1H),3.69 (d, J = 17.2 Hz, 1H), 2.49 (s, 3H). 5-456 (B) δ 7.61 (s, 2H),7.45-7.55 (m, 2H), 7.39 (d, J = 7.9 Hz, 1H), 6.28 (t, J = 6.6 Hz, 1H),6.24 (bs, 1H), 4.0-4.15 (m, 2H), 4.07 (d, J = 17.2 Hz, 1H), 3.69 (d, J =17.2 Hz, 1H), 2.43 (s, 3H), 1.50 (s, 9H). 5-457 (B) δ 8.5-8.55 (m, 1H),7.71 (td, J = 7.7, 1.7 Hz, 1H), 7.62 (s, 2H), 7.45-7.55 (m, 3H), 7.34(d, J = 7.9 Hz, 1H), 7.29 (t, J = 4.8 Hz, 1H), 7.2-7.25 (m, 1H), 6.37(bs, 1H), 4.75 (d, J = 5.0 Hz, 2H), 4.07 (d, J = 17.2 Hz, 1H), 3.70 (d,J = 17.2 Hz, 1H), 2.50 (s, 3H), 1.50 (s, 9H). 5-460 (B) δ 8.77 (d, J =2.0 Hz, 1H), 7.71 (d, J = 2.2 Hz, 1H), 7.3-7.55 (m, 6H), 6.67 (t, J =5.5 Hz, 1H), 4.76 (d, J = 5.7 Hz, 2H), 4.07 (d, J = 17.2 Hz, 1H), 3.69(d, J = 17.2 Hz, 1H), 2.44 (s, 3H). 5-461 (B) δ 8.5-8.55 (m, 1H),7.5-7.75 (m, 6H), 7.45 (dd, J = 8.6, 2.0 Hz, 1H), 7.35 (d, J = 7.9 Hz,1H), 7.29 (t, J = 4.8 Hz, 1H), 7.15-7.3 (m, 1H), 4.75 (d, J = 4.8 Hz,2H), 4.09 (d, J = 17.2 Hz, 1H), 3.71 (d, J = 17.2 Hz, 1H), 2.72 (s, 3H).5-462 (B) δ 7.83 (d, J = 8.1 Hz, 1H), 7.74 (d, J = 1.7 Hz, 1H), 7.62(dd, J = 8.1, 1.7 Hz, 1H), 7.5-7.55 (m, 2H), 7.44 (t, J = 1.8 Hz, 1H),6.48 (bs, 2H), 4.08 (d, J = 17.2 Hz, 1H), 3.71 (d, J = 17.2 Hz, 1H).5-463 (B) δ 7.45-7.55 (m, 5H), 7.43 (t, J = 1.8 Hz, 1H), 7.27 (t, J =5.1 Hz, 1H), 7.21 (bs, 1H), 4.27 (d, J = 5.1 Hz, 2H), 4.07 (d, J = 17.2Hz, 1H), 3.9-4.0 (m, 2H), 3.70 (d, J = 17.2 Hz, 1H). 5-468 (B) δ 8.16(d, J = 1.7 Hz, 1H), 7.69 (dd, J = 8.1, 1.7 Hz, 1H), 7.5-7.55 (m, 2H),7.43 (t, J = 1.8 Hz, 1H), 7.42 (d, J = 8.1 Hz, 1H), 7.21 (t, J = 5.3 Hz,1H), 7.03 (bs, 1H), 4.24 (d, J = 5.3 Hz, 2H), 4.07 (d, J = 17.2 Hz, 1H),3.9-4.0 (m, 2H), 3.70 (d, J = 17.2 Hz, 1H). 5-470 (B) δ 9.22 (bs, 1H),8.40 (s, 2H), 8.11 (d, J = 1.6 Hz, 1H), 7.74 (dd, J = 8.1, 1.6 Hz, 1H),7.45-7.55 (m, 3H), 7.44 (t, J = 1.8 Hz, 1H), 4.08 (d, J = 17.2 Hz, 1H),3.71 (d, J = 17.2 Hz, 1H). 5-471 (A) δ 7.35-7.6 (m, 6H), 5.87 (bs, 1H),4.08 (d, J = 17.1 Hz, 1H), 3.69 (d, J = 17.1 Hz, 1H), 3.01 (d, J = 4.8Hz, 3H), 2.47 (s, 3H). 5-472 (B) δ 7.5-7.55 (m, 4H), 7.4-7.5 (m, 2H),5.8-6.15 (m, 1H), 4.08 (d, J = 17.2 Hz, 1H), 3.84 (tdd, J = 15.0, 6.0,4.2 Hz, 2H), 3.70 (d, J = 17.2 Hz, 1H), 2.48 (s, 3H). 5-473 (B) δ7.4-7.55 (m, 6H), 6.42 (bs, 1H), 4.87 (d, J = 6.8 Hz, 2H), 4.09 (d, J =17.4 Hz, 1H), 3.70 (d, J = 17.4 Hz, 1H), 3.45 (s, 3H), 2.50 (s, 3H).5-474 (B) δ 7.4-7.55 (m, 6H), 6.46 (bs, 1H), 4.92 (d, J = 6.8 Hz, 2H),4.08 (d, J = 17.4 Hz, 1H), 3.6-3.75 (m, 3H), 2.49 (s, 3H), 1.25 (t, J =6.8 Hz, 3H). 5-475 (B) δ 7.5-7.55 (m, 4H), 7.4-7.5 (m, 2H), 6.40 (bs,1H), 4.92 (d, J = 6.8 Hz, 2H), 4.09 (d, J = 17.4 Hz, 1H), 3.70 (d, J =17.4 Hz, 1H), 3.57 (t, J = 6.6 Hz, 2H), 2.50 (s, 3H), 1.55-1.7 (m, 2H),0.95 (t, J = 7.4 Hz, 3H). 5-476 (B) δ 7.4-7.55 (m, 6H), 6.51 (bs, 1H),4.92 (d, J = 6.6 Hz, 2H), 4.09 (d, J = 17.4 Hz, 1H), 3.90 (sep, J = 6.0Hz, 1H), 3.71 (d, J = 17.4 Hz, 1H), 2.47 (s, 3H), 1.22 (d, J = 6.0 Hz,6H). 5-477 (B) δ 7.4-7.55 (m, 6H), 6.50 (t, J = 7.2 Hz, 1H), 4.98 (d, J= 6.8 Hz, 2H), 4.09 (d, J = 17.4 Hz, 1H), 3.85-3.95 (m, 2H), 3.70 (d, J= 17.4 Hz, 1H), 2.50 (s, 3H), 1.95-2.05 (m, 2H). 5-478 (B) δ 7.4-7.6 (m,6H), 6.35-6.55 (m, 1H), 5.75-6.05 (m, 1H), 4.96 (dd, J = 28.0, 7.2 Hz,2H), 4.09 (d, J = 17.4 Hz, 1H), 3.65-4.2 (m, 3H), 2.50 (s, 3H). 5-479(B) δ 7.45-7.55 (m, 6H), 6.56 (t, J = 7.2 Hz, 1H), 5.82 (t, J = 5.6 Hz,1H), 5.34 (t, J = 5.6 Hz, 1H), 5.03 (d, J = 5.6 Hz, 2H), 4.09 (d, J =17.4 Hz, 1H), 3.70 (d, J = 17.4 Hz, 1H), 2.51 (s, 3H), 2.30 (t, J = 7.4Hz, 1H). 5-481 (B) δ 7.4-7.6 (m, 6H), 6.65 (t, J = 7.2 Hz, 1H), 5.17 (d,J = 5.6 Hz, 2H), 4.37 (s, 2H), 4.09 (d, J = 17.4 Hz, 1H), 3.70 (d, J =17.4 Hz, 1H), 2.51 (s, 3H). 5-482 (B) δ 7.4-7.6 (m, 6H), 6.63 (bs, 1H),4.97 (d, J = 6.4 Hz, 2H), 4.09 (d, J = 17.4 Hz, 1H), 3.25-3.8 (m, 8H),2.50 (s, 3H). 5-483 (B) δ 7.4-7.6 (m, 6H), 6.41 (t, J = 7.2 Hz, 1H),5.85-6.0 (m, 2H), 5.2-5.5 (m, 3H), 4.95 (d, J = 7.2 Hz, 1H), 4.05-4.2(m, 2H), 3.70 (d, J = 17.4 Hz, 1H), 2.50 (s, 3H). 5-484 (B) δ 7.4-7.55(m, 6H), 6.51 (t, J = 7.2 Hz, 1H), 5.01 (d, J = 7.2 Hz, 2H), 4.32 (d, J= 2.4 Hz, 2H), 4.09 (d, J = 17.4 Hz, 1H), 3.70 (t, J = 17.4 Hz, 1H),2.51 (s, 3H), 2.47 (t, J = 2.4 Hz, 1H). 5-485 (B) δ 7.25-7.55 (m, 11H),6.43 (bs, 1H), 5.01 (d, J = 6.8 Hz, 2H), 4.65-4.75 (m, 2H), 4.08 (d, J =17.4 Hz, 1H), 3.70 (d, J = 17.4 Hz, 1H), 2.50 (s, 3H). 5-486 (B) δ7.5-7.55 (m, 4H), 7.4-7.45 (m, 2H), 6.95 (t, J = 7.2 Hz, 1H), 5.41 (d, J= 7.2 Hz, 2H), 4.08 (d, J = 17.4 Hz, 1H), 3.70 (d, J = 17.4 Hz, 1H),2.48 (s, 3H), 2.12 (s, 3H). 5-487 (A) δ 7.45-7.55 (m, 4H), 7.4-7.45 (m,2H), 6.44 (bs, 1H), 5.6-5.7 (m, 1H), 4.0-4.15 (m, 2H), 3.70 (d, J = 17.4Hz, 1H), 2.48 (s, 3H), 1.45 (d, J = 6.0 Hz, 3H). 5-488 (A) δ 7.4-7.6 (m,6H), 6.18 (d, J = 9.4 Hz, 1H), 5.6-5.7 (m, 1H), 4.0-4.2 (m, 3H), 3.71(d, J = 17.4 Hz, 1H), 2.48 (s, 3H), 1.51 (d, J = 6.0 Hz, 3H). 5-490 (B)δ 7.45-7.55 (m, 5H), 7.43 (t, J = 1.8 Hz, 1H), 6.57 (t, J = 4.8 Hz, 1H),4.09 (d, J = 17.2 Hz, 1H), 3.71 (d, J = 17.2 Hz, 1H), 3.55-3.7 (m, 10H),3.45-3.5 (m, 2H), 3.25 (s, 3H), 2.47 (s, 3H). 5-492 (A) δ 7.45-7.65 (m,6H), 5.87 (d, J = 8.4 Hz, 1H), 4.4-4.55 (m, 1H), 4.18 (d, J = 6.9 Hz,2H), 4.08 (d, J = 17.4 Hz, 1H), 3.69 (d, J = 17.4 Hz, 1H), 2.47 (s, 3H),2.10 (s, 3H), 1.29 (d, J = 6.9 Hz, 3H). 5-493 (B) δ 7.35-7.55 (m, 6H),6.21 (d, J = 5.8 Hz, 1H), 5.27 (bs, 1H), 5.10 (bs, 1H), 4.44 (bs, 1H),4.0-4.25 (m, 3H), 3.5-3.75 (m, 4H), 2.46 (s, 3H), 1.25-1.3 (m, 3H).5-495 (A) δ 7.3-7.55 (m, 6H), 6.4-6.5 (m, 1H), 4.55-4.7 (m, 1H),3.65-4.15 (m, 6H), 2.39 (s, 3H), 2.2-2.45 (m, 1H), 1.8-2.0 (m, 1H).5-496 (A) δ 7.4-7.6 (m, 6H), 6.38 (d, J = 9.0 Hz, 1H), 5.2-5.35 (m, 1H),4.09 (d, J = 17.4 Hz, 1H), 3.95-4.15 (m, 1H), 3.71 (d, J = 17.4 Hz, 1H),3.6-3.75 (m, 1H), 2.46 (s, 3H), 1.85-2.0 (m, 2H), 1.4-1.75 (m, 4H).5-497 (A) δ 7.5-7.6 (m, 4H), 7.4-7.45 (m, 2H), 6.10 (bs, 1H), 4.55 (d, J= 6.8 Hz, 2H), 4.08 (d, J = 17.4 Hz, 1H), 3.70 (d, J = 17.4 Hz, 1H),2.49 (s, 3H), 2.26 (s, 3H). 5-500 (B) δ 7.5-7.6 (m, 4H), 7.43 (t, J =1.8 Hz, 1H), 7.39 (d, J = 7.7 Hz, 1H), 6.70 (t, J = 6.8 Hz, 1H), 4.83(d, J = 6.8 Hz, 2H), 4.07 (d, J = 17.2 Hz, 1H), 3.69 (d, J = 17.2 Hz,1H), 2.46 (s, 3H), 2.40 (s, 3H). 5-501 (B) δ 7.5-7.55 (m, 4H), 7.42 (t,J = 1.8 Hz, 1H), 7.41 (d, J = 8.8 Hz, 1H), 7.20 (t, J = 6.8 Hz, 1H),5.11 (d, J = 6.8 Hz, 2H), 4.67 (q, J = 7.2 Hz, 2H), 4.09 (d, J = 17.2Hz, 1H), 3.73 (d, J = 17.2 Hz, 1H), 2.46 (s, 3H), 1.44 (t, J = 7.2 Hz,3H). 5-502 (B) δ 7.4-7.55 (m, 6H), 6.6-6.65 (m, 1H), 4.56 (d, J = 6.4Hz, 2H), 4.08 (d, J = 17.4 Hz, 1H), 3.70 (d, J = 17.4 Hz, 1H), 3.15 (q,J = 7.2 Hz, 6H), 2.51 (s, 3H), 1.37 (t, J = 7.2 Hz, 9H). 5-504 (B) δ7.80 (bs, 1H), 7.45-7.55 (m, 3H), 7.43 (t, J = 1.8 Hz, 1H), 7.3-7.4 (m,4H), 6.95-7.05 (m, 2H), 6.59 (t, J = 5.3 Hz, 1H), 4.05 (d, J = 17.2 Hz,1H), 3.65-3.75 (m, 2H), 3.68 (d, J = 17.2 Hz, 1H), 3.22 (t, J = 6.4 Hz,2H), 2.44 (s, 3H). 5-505 (B) δ 8.47 (d, J = 4.8 Hz, 2H), 7.45-7.55 (m,4H), 7.43 (t, J = 1.8 Hz, 1H), 7.34 (d, J = 8.4 Hz, 1H), 7.00 (t, J =4.8 Hz, 1H), 6.85 (t, J = 5.3 Hz, 1H), 4.08 (d, J = 17.2 Hz, 1H), 3.81(td, J = 6.2, 5.3 Hz, 2H), 3.71 (d, J = 17.2 Hz, 1H), 3.43 (t, J = 6.2Hz, 2H), 2.44 (s, 3H). 5-506 (B) δ 8.96 (d, J = 5.0 Hz, 2H), 7.61 (t, J= 5.0 Hz, 1H), 7.45-7.55 (m, 5H), 7.43 (t, J = 1.8 Hz, 1H), 6.75 (t, J =5.7 Hz, 1H), 4.08 (d, J = 17.2 Hz, 1H), 3.95-4.1 (m, 2H), 3.85-3.95 (m,2H), 3.70 (d, J = 17.2 Hz, 1H), 2.48 (s, 3H). 5-508 (B) δ 7.5-7.55 (m,4H), 7.4-7.45 (m, 2H), 6.24 (bs, 1H), 4.39 (d, J = 6.8 Hz, 2H), 4.08 (d,J = 17.4 Hz, 1H), 3.70 (d, J = 17.4 Hz, 1H), 2.76 (q, J = 7.2 Hz, 2H),2.49 (s, 3H), 1.15 (t, J = 7.2 Hz, 3H). 5-509 (A) δ 7.5-7.55 (m, 5H),7.35-7.5 (m, 2H), 6.37 (bs, 1H), 4.44 (t, J = 6.6 Hz, 2H), 4.09 (d, J =17.4 Hz, 1H), 3.70 (d, J = 17.4 Hz, 1H), 3.2-3.4 (m, 2H), 2.48 (s, 3H).5-510 (B) δ 7.45-7.55 (m, 4H), 7.35-7.45 (m, 2H), 7.04 (bs, 1H), 4.92(d, J = 6.8 Hz, 2H), 4.44 (q, J = 8.8 Hz, 2H), 4.08 (d, J = 17.4 Hz,1H), 3.69 (d, J = 17.4 Hz, 1H), 2.46 (s, 3H), 2.18 (s, 3H). 5-511 (B) δ7.5-7.55 (m, 4H), 7.35-7.45 (m, 2H), 6.89 (bs, 1H), 4.91 (d, J = 6.8 Hz,2H), 4.15-4.3 (m, 2H), 4.08 (d, J = 17.4 Hz, 1H), 3.78 (s, 3H), 3.70 (d,J = 17.4 Hz, 1H), 2.18 (s, 3H). 5-521 (B) δ 7.4-7.55 (m, 6H), 6.70 (bs,1H), 5.2-5.3 (m, 1H), 4.03 (d, J = 17.4 Hz, 1H), 3.72 (d, J = 17.4 Hz,1H), 3.5-3.6 (m, 2H), 3.3-3.4 (m, 2H), 3.03 (q, J = 7.4 Hz, 2H), 2.41(s, 3H), 1.34 (t, J = 7.2 Hz, 3H). 5-522 (B) δ 7.65 (t, J = 4.0 Hz, 1H),7.4-7.6 (m, 6H), 6.23 (bs, 1H), 4.40 (q, J = 8.4 Hz, 2H), 4.25-4.3 (m,2H), 4.09 (d, J = 17.4 Hz, 1H), 3.71 (d, J = 17.4 Hz, 1H), 2.50 (s, 3H).5-523 (A) δ 7.3-7.7 (m, 7H), 6.44 (d, J = 7.5 Hz, 1H), 4.75-4.9 (m, 1H),4.09 (d, J = 17.4 Hz, 1H), 3.84 (s, 3H), 3.71 (d, J = 17.4 Hz, 1H), 2.47(s, 3H), 1.44 (d, J = 6.9 Hz, 3H). 5-524 (A) δ 7.4-7.65 (m, 7H), 6.79(d, J = 7.3 Hz, 1H), 4.8-4.9 (m, 1H), 4.05-4.2 (m, 3H), 3.83 (s, 3H),3.69 (d, J = 17.4 Hz, 1H), 2.49 (s, 3H). 5-525 (B) δ 7.35-7.55 (m, 6H),6.15 (bs, 1H), 4.05-4.2 (m, 3H), 3.70 (d, J = 17.2 Hz, 1H), 3.49 (q, J =6.4 Hz, 2H), 2.4-2.5 (m, 5H), 1.9-2.0 (m, 2H), 1.2-1.3 (m, 3H). 5-527(B) δ 7.45-7.6 (m, 5H), 7.4-7.45 (m, 1H), 7.07 (bs, 1H), 4.05-4.3 (m,3H), 3.74 (d, J = 17.4 Hz, 1H), 3.35 and 3.47 (q, J = 6.8 Hz, 2H), 2.98and 3.00 (s, 3H), 2.49 (s, 3H), 1.1-1.3 (m, 3H). 5-528 (B) δ 7.4-7.6 (m,6H), 7.04 (bs, 1H), 4.24 (d, J = 4.0 Hz, 2H), 4.10 (d, J = 17.4 Hz, 1H),3.72 (d, J = 17.4 Hz, 1H), 3.44 (q, J = 6.8 Hz, 2H), 3.33 (q, J = 6.8Hz, 2H), 2.50 (s, 3H), 1.24 (t, J = 6.8 Hz, 3H), 1.18 (t, J = 6.8 Hz,3H). 5-532 (A) δ 7.4-7.55 (m, 5H), 7.2-7.25 (m, 1H), 6.66 (bs, 1H), 6.16(bs, 1H), 4.53 (t, J = 5.0 Hz, 1H), 4.1-4.15 (m, 3H), 3.65-3.75 (m, 3H),3.5-3.6 (m, 2H), 3.46 (t, J = 5.0 Hz, 2H), 2.48 (s, 3H), 1.22 (t, J =6.8 Hz, 6H). 5-538 (B) δ 7.4-7.55 (m, 6H), 6.63 (d, J = 7.8 Hz, 1H),6.29 (bs, 1H), 5.62 (bs, 1H), 4.6-4.8 (m, 1H), 4.08 (d, J = 17.4 Hz,1H), 3.70 (d, J = 17.4 Hz, 1H), 2.46 (s, 3H), 1.51 (d, J = 7.0 Hz, 3H).5-546 (A) δ 7.35-7.6 (m, 5H), 7.15-7.3 (m, 1H), 6.95-7.1 (m, 1H),6.6-6.8 (m, 2H), 5.52 (bs, 1H), 4.44 (bs, 1H), 4.05 (d, J = 17.3 Hz,1H), 3.75 (s, 3H), 3.65 (d, J = 17.3 Hz, 1H), 2.65-3.2 (m, 4H), 2.39 (s,3H), 1.2-2.2 (m, 4H). 5-548 (A) δ 7.85 (bs, 1H), 7.45-7.55 (m, 6H), 7.03(t, J = 6.6 Hz, 1H), 6.56 (s, 1H), 5.72 (d, J = 6.6 Hz, 2H), 4.07 (d, J= 17.3 Hz, 1H), 3.68 (d, J = 17.3 Hz, 1H), 2.39 (s, 3H). 5-555 (B) δ7.4-7.6 (m, 6H), 7.14 (s, 1H), 6.45 (bs, 1H), 4.6-4.7 (m, 2H), 4.08 (d,J = 19.0 Hz, 1H), 3.70 (d, J = 19.0 Hz, 1H), 2.67 (s, 3H), 2.45 (s, 3H).5-556 (B) δ 7.67 (s, 1H), 7.4-7.5 (m, 6H), 6.70 (bs, 1H), 4.75-4.8 (m,2H), 4.08 (d, J = 19.0 Hz, 1H), 3.70 (d, J = 19.0 Hz, 1H), 3.29 (s, 3H),2.44 (s, 3H). 5-557 (A) δ 7.4-7.6 (m, 7H), 6.51 (t, J = 6.0 Hz, 1H),4.77 (dd, J = 6.0, 0.6 Hz, 2H), 4.08 (d, J = 17.2 Hz, 1H), 3.69 (d, J =17.2 Hz, 1H), 2.45 (s, 3H). 5-558 (B) δ 8.59 (s, 1H), 7.45-7.55 (m, 5H),7.43 (t, J = 1.8 Hz, 1H), 6.81 (t, J = 5.5 Hz, 1H), 4.90 (d, J = 5.7 Hz,2H), 4.09 (d, J = 17.2 Hz, 1H), 3.72 (d, J = 17.2 Hz, 1H), 2.45 (s, 3H).5-559 (B) δ 8.0-8.05 (m, 2H), 7.35-7.6 (m, 9H), 6.29 (d, J = 6.8 Hz,2H), 4.05 (d, J = 17.4 Hz, 1H), 3.67 (d, J = 17.4 Hz, 1H), 2.38 (s, 3H).5-560 (A) δ 7.25-7.7 (m, 8H), 6.99 (d, J = 8.6 Hz, 1H), 6.35-6.5 (m,1H), 6.25 (bs, 1H), 4.06 (d, J = 17.4 Hz, 1H), 3.68 (d, J = 17.4 Hz,1H), 2.33 (s, 3H), 1.84 (s, 3H). 5-561 (B) δ 8.75 (bs, 1H), 7.45-7.55(m, 4H), 7.43 (t, J = 1.8 Hz, 1H), 7.36 (d, J = 8.1 Hz, 1H), 4.08 (d, J= 17.2 Hz, 1H), 3.89 (s, 3H), 3.70 (d, J = 17.2 Hz, 1H), 2.43 (s, 3H).5-563 (B) δ 7.5-7.6 (m, 5H), 7.44 (t, J = 1.8 Hz, 1H), 4.09 (d, J = 17.4Hz, 1H), 3.71 (d, J = 17.4 Hz, 1H), 3.41 (s, 3H), 2.52 (s, 3H). 5-564(B) δ 8.74 (s, 1H), 7.45-7.6 (m, 5H), 7.43 (t, J = 1.8 Hz, 1H), 4.09 (d,J = 17.2 Hz, 1H), 3.72 (d, J = 17.2 Hz, 1H), 3.04 (s, 6H), 2.51 (s, 3H).5-565 (A) δ 8.23 (bs, 1H), 7.35-7.65 (m, 11H), 4.10 (s, 2H), 4.07 (d, J= 17.4 Hz, 1H), 3.70 (d, J = 17.4 Hz, 1H), 2.46 (s, 3H). 5-572 (B) δ8.10 (s, 1H), 7.45-7.6 (m, 5H), 7.43 (d, J = 8.1 Hz, 1H), 5.20 (tqui, J= 20.1, 4.4 Hz, 1H), 4.5-4.75 (m, 4H), 4.09 (d, J = 17.2 Hz, 1H), 3.71(d, J = 17.2 Hz, 1H), 2.48 (s, 3H). 5-573 (B) δ 8.15 (bs, 1H), 7.45-7.6(m, 4H), 7.46 (d, J = 8.4 Hz, 1H), 7.43 (t, J = 1.8 Hz, 1H), 5.05-5.25(m, 1H), 4.55-4.75 (m, 2H), 4.09 (d, J = 17.2 Hz, 1H), 3.65-3.8 (m, 3H),2.47 (s, 3H). 5-575 (B) δ 8.87 (bs, 1H), 7.4-7.55 (m, 6H), 4.08 (d, J =17.2 Hz, 1H), 3.70 (d, J = 17.2 Hz, 1H), 3.04 (bs, 6H), 2.44 (s, 3H).5-581 (A) δ 9.27 (t, J = 5.5 Hz, 1H), 8.74 (s, 1H), 8.59 (d, J = 5.0 Hz,1H), 7.4-7.7 (m, 7H), 7.15-7.3 (m, 2H), 4.65 (d, J = 5.5 Hz, 2H), 4.08(d, J = 17.3 Hz, 1H), 3.70 (d, J = 17.3 Hz, 1H), 2.53 (s, 3H). 5-583 (B)δ 8.47 (bs, 1H), 7.4-7.55 (m, 6H), 4.08 (d, J = 17.2 Hz, 1H), 3.70 (d, J= 17.2 Hz, 1H), 3.4-3.55 (m, 4H), 2.44 (s, 3H), 1.9-2.05 (m, 4H). 5-585(A) δ 7.3-7.7 (m, 11H), 7.18 (t, J = 7.2 Hz, 1H), 4.10 (d, J = 17.4 Hz,1H), 3.72 (d, J = 17.4 Hz, 1H), 2.54 (s, 3H). 5-588 (A) δ 7.5-7.65 (m,7H), 7.4-7.45 (m, 2H), 7.08 (t, J = 8.4 Hz, 2H), 4.10 (d, J = 17.3 Hz,1H), 3.72 (d, J = 17.3 Hz, 1H), 2.53 (s, 3H). 5-591 (A) δ 8.20 (bs, 1H),7.85 (s, 1H), 7.4-7.6 (m, 6H), 6.9-7.25 (m, 4H), 4.10 (d, J = 17.0 Hz,1H), 3.72 (d, J = 17.0 Hz, 1H), 2.55 (s, 3H). 5-601 (A) δ 8.04 (s, 1H),7.81 (d, J = 6.9 Hz, 1H), 7.4-7.65 (m, 9H), 4.10 (d, J = 17.1 Hz, 1H),3.72 (d, J = 17.1 Hz, 1H), 2.54 (s, 3H). 5-603 (A) δ 8.77 (d, J = 7.4Hz, 1H), 7.4-7.7 (m, 9H), 7.14 (t, J = 7.4 Hz, 1H), 6.05 (d, J = 6.9 Hz,1H), 4.15-4.3 (m, 1H), 4.10 (d, J = 17.3 Hz, 1H), 3.71 (d, J = 17.3 Hz,1H), 2.58 (s, 3H), 1.25 (d, J = 6.9 Hz, 6H). 5-604 (A) δ 7.4-7.6 (m,7H), 6.85-7.0 (m, 2H), 6.65-6.85 (m, 1H), 4.11 (d, J = 17.1 Hz, 1H),3.72 (d, J = 17.1 Hz, 1H), 2.55 (s, 3H). 5-605 (A) δ 8.25-8.4 (m, 1H),7.7-7.75 (m, 1H), 7.55-7.6 (m, 3H), 7.5-7.55 (m, 2H), 7.4-7.45 (m, 1H),7.05-7.15 (m, 1H), 6.7-6.85 (m, 1H), 4.10 (d, J = 17.4 Hz, 1H), 3.72 (d,J = 17.4 Hz, 1H), 2.55 (s, 3H). 5-609 (A) δ 7.89 (s, 1H), 7.2-7.7 (m,9H), 4.10 (d, J = 17.1 Hz, 1H), 3.71 (d, J = 17.1 Hz, 1H), 2.53 (s, 3H).5-610 (A) δ 7.45-7.65 (m, 8H), 7.44 (s, 1H), 7.17 (s, 1H), 4.10 (d, J =17.4 Hz, 1H), 3.72 (d, J = 17.4 Hz, 1H), 2.52 (s, 3H). 5-611 (A) δ 8.36(dd, J = 6.3, 2.7 Hz, 1H), 7.9-8.05 (m, 1H), 7.80 (s, 1H), 7.4-7.6 (m,6H), 7.32 (t, J = 9.0 Hz, 1H), 4.11 (d, J = 17.3 Hz, 1H), 3.73 (d, J =17.3 Hz, 1H), 2.52 (s, 3H). 5-612 (A) δ 7.5-7.7 (m, 5H), 7.44 (t, J =2.0 Hz, 1H), 7.03 (bs, 1H), 6.80 (t, J = 7.2 Hz, 2H), 4.11 (d, J = 17.4Hz, 1H), 3.72 (d, J = 17.4 Hz, 1H), 2.54 (s, 3H). 5-615 (A) δ 8.41 (bs,1H), 7.4-7.65 (m, 6H), 6.74 (bs, 2H), 6.23 (bs, 2H), 4.09 (d, J = 17.0Hz, 1H), 3.73 (d, J = 17.0 Hz, 1H), 2.53 (s, 3H). 5-617 (A) δ 7.4-7.75(m, 9H), 6.38 (bs, 1H), 4.08 (d, J = 17.3 Hz, 1H), 3.70 (d, J = 17.3 Hz,1H), 2.53 (s, 3H). 5-618 (A) δ 9.23 (bs, 1H), 7.4-7.7 (m, 8H), 4.10 (d,J = 17.3 Hz, 1H), 3.72 (d, J = 17.4 Hz, 1H), 2.53 (s, 3H). 5-619 (B) δ9.32 (bs, 1H), 7.45-7.7 (m, 7H), 4.11 (d, J = 17.2 Hz, 1H), 3.73 (d, J =17.2 Hz, 1H), 2.60 (s, 3H). 5-621 (B) δ 7.4-7.55 (m, 6H), 6.80 (bs, 1H),4.56 (d, J = 6.4 Hz, 2H), 4.09 (d, J = 17.0 Hz, 1H), 3.71 (d, J = 17.0Hz, 1H), 3.16 (q, J = 7.2 Hz, 6H), 2.51 (s, 3H), 1.37 (t, J = 7.2 Hz,9H). 5-629 (A) δ 8.4-8.6 (m, 3H), 7.95-8.1 (m, 1H), 7.61 (s, 3H),7.4-7.55 (m, 3H), 4.12 (d, J = 17.1 Hz, 1H), 3.73 (d, J = 17.1 Hz, 1H),2.56 (s, 3H). 5-630 (A) δ 8.29 (d, J = 7.8 Hz, 1H), 8.23 (s, 1H), 7.74(t, J = 7.8 Hz, 1H), 7.5-7.6 (m, 6H), 7.13 (d, J = 7.2 Hz, 1H), 4.11 (d,J = 17.1 Hz, 1H), 3.73 (d, J = 17.1 Hz, 1H), 2.55 (s, 3H). 5-631 (A) δ8.32 (d, J = 8.1 Hz, 1H), 8.21 (s, 1H), 7.2-7.7 (m, 8H), 4.11 (d, J =17.4 Hz, 1H), 3.73 (d, J = 17.4 Hz, 1H), 2.55 (s, 3H). 5-633 (A) δ 8.46(s, 1H), 8.27 (d, J = 7.1 Hz, 1H), 7.76 (s, 1H), 7.3-7.6 (m, 7H), 4.10(d, J = 17.0 Hz, 1H), 3.72 (d, J = 17.0 Hz, 1H), 2.52 (s, 3H). 5-634 (A)δ 8.72 (d, J = 2.4 Hz, 1H), 8.52 (dd, J = 8.4, 2.4 Hz, 1H), 7.99 (s,1H), 7.73 (d, J = 8.4 Hz, 1H), 7.4-7.65 (m, 6H), 4.11 (d, J = 17.3 Hz,1H), 3.73 (d, J = 17.3 Hz, 1H), 2.54 (s, 3H). 5-635 (A) δ 8.31 (d, J =5.4 Hz, 1H), 7.81 (s, 1H), 7.75-7.8 (m, 1H), 7.4-7.6 (m, 7H), 4.10 (d, J= 17.4 Hz, 1H), 3.72 (d, J = 17.4 Hz, 1H), 2.53 (s, 3H). 5-637 (A) δ8.82 (s, 1H), 8.41 (d, J = 4.8 Hz, 1H), 7.4-7.6 (m, 6H), 6.90 (d, J =4.8 Hz, 1H), 4.11 (d, J = 17.4 Hz, 1H), 3.73 (d, J = 17.4 Hz, 1H), 2.53(s, 3H), 2.45 (s, 3H). 5-647 (B) δ 7.4-7.55 (m, 4H), 7.37 (d, J = 7.9Hz, 1H), 6.37 (t, J = 6.0 Hz, 1H), 4.0-4.15 (m, 2H), 4.06 (d, J = 17.2Hz, 1H), 3.70 (d, J = 17.2 Hz, 1H), 2.48 (s, 3H), 2.41 (s, 3H). 5-648(B) δ 8.5-8.6 (m, 1H), 7.71 (td, J = 7.7, 1.8 Hz, 1H), 7.45-7.6 (m, 6H),7.38 (d, J = 7.9 Hz, 1H), 7.2-7.3 (m, 1H), 4.73 (d, J = 5.1 Hz, 2H),4.07 (d, J = 17.2 Hz, 1H), 3.71 (d, J = 17.2 Hz, 1H), 2.71 (s, 3H), 2.47(s, 3H). 5-649 (B) δ 8.55-8.65 (m, 1H), 7.84 (td, J = 7.7, 1.7 Hz, 1H),7.3-7.8 (m, 8H), 4.78 (d, J = 5.1 Hz, 2H), 4.05 (d, J = 17.2 Hz, 1H),3.71 (d, J = 17.2 Hz, 1H), 3.56 (bs, 1H), 2.49 (s, 3H). 5-651 (B) δ8.5-8.55 (m, 1H), 7.71 (td, J = 7.8, 1.8 Hz, 1H), 7.5-7.6 (m, 5H), 7.34(d, J = 7.9 Hz, 1H), 7.2-7.3 (m, 2H), 4.75 (d, J = 4.8 Hz, 2H), 4.05 (d,J = 17.2 Hz, 1H), 3.92 (s, 3H), 3.71 (d, J = 17.2 Hz, 1H), 2.49 (s, 3H).5-652 (B) δ 8.5-8.6 (m, 1H), 7.92 (td, J = 7.7, 1.8 Hz, 1H), 7.45-7.7(m, 6H), 7.39 (d, J = 7.7 Hz, 1H), 7.15-7.3 (m, 1H), 4.71 (d, J = 5.3Hz, 2H), 4.08 (d, J = 17.2 Hz, 1H), 3.73 (d, J = 17.2 Hz, 1H), 2.46 (s,3H), 1.57 (s, 9H). 5-653 (B) δ 7.4-7.55 (m, 4H), 7.39 (d, J = 7.9 Hz,1H), 6.37 (t, J = 5.9 Hz, 1H), 4.0-4.15 (m, 2H), 4.05 (d, J = 17.2 Hz,1H), 3.69 (d, J = 17.2 Hz, 1H), 2.90 (s, 6H), 2.42 (s, 3H). 5-654 (B) δ8.5-8.6 (m, 1H), 7.71 (td, J = 7.7, 1.8 Hz, 1H), 7.45-7.55 (m, 5H), 7.41(t, J = 4.8 Hz, 1H), 7.36 (d, J = 7.7 Hz, 1H), 7.2-7.3 (m, 1H), 4.73 (d,J = 5.0 Hz, 2H), 4.05 (d, J = 17.2 Hz, 1H), 3.70 (d, J = 17.2 Hz, 1H),2.90 (s, 6H), 2.48 (s, 3H). 5-655 (A) δ 8.12 (s, 1H), 7.7-7.75 (m, 1H),7.4-7.5 (m, 4H), 6.73 (bs, 1H), 5.03 (d, J = 6.8 Hz, 2H), 4.13 (q, J =8.4 Hz, 2H), 4.07 (d, J = 17.4 Hz, 1H), 3.69 (d, J = 17.4 Hz, 1H). 5-656(A) δ 8.09 (bs, 1H), 7.35-7.75 (m, 5H), 6.27 (bs, 1H), 5.8-5.9 (m, 1H),3.8-4.2 (m, 3H), 3.69 (d, J = 17.4 Hz, 1H), 2.2-2.35 (m, 1H), 1.9-2.1(m, 3H). 5-657 (B) δ 8.37 (d, J = 1.7 Hz, 1H), 7.83 (dd, J = 8.1, 1.8Hz, 1H), 7.51 (bs, 2H), 7.45 (t, J = 1.8 Hz, 1H), 7.43 (d, J = 8.1 Hz,1H), 7.35 (bs, 1H), 6.99 (bs, 1H), 4.23 (d, J = 17.8 Hz, 1H), 4.22 (d, J= 5.1 Hz, 2H), 3.9-4.05 (m, 2H), 3.84 (d, J = 17.8 Hz, 1H). 5-658 (A) δ7.4-7.6 (m, 6H), 5.9-6.0 (m, 2H), 4.9-5.0 (m, 1H), 4.11 (d, J = 17.4 Hz,1H), 3.73 (d, J = 17.4 Hz, 1H), 3.53 (s, 3H), 2.33 (s, 3H), 2.1-2.45 (m,3H), 1.95-2.05 (m, 1H), 1.6-1.8 (m, 2H). 5-662 (A) δ 8.41 (s, 1H),7.4-7.55 (m, 6H), 5.67 (t, J = 6.3 Hz, 1H), 4.12 (d, J = 17.4 Hz, 1H),3.7-3.9 (m, 2H), 3.72 (d, J = 17.4 Hz, 1H), 3.19 (s, 3H), 2.47 (s, 3H).5-667 (A) δ 8.78 (bs, 1H), 7.75 (s, 1H), 7.45-7.6 (m, 5H), 7.43 (t, J =1.5 Hz, 1H), 4.10 (d, J = 17.4 Hz, 1H), 3.73 (d, J = 17.4 Hz, 1H), 2.51(s, 3H). 5-668 (A) δ 8.38 (dd, J = 4.8, 1.5 Hz, 1H), 8.04 (s, 1H), 7.77(dd, J = 7.8, 1.5 Hz, 1H), 7.65-7.65 (m, 5H), 7.57 (t, J = 1.8 Hz, 1H),7.12 (dd, J = 7.8, 4.8 Hz, 1H), 4.10 (d, J = 17.1 Hz, 1H), 3.71 (d, J =17.1 Hz, 1H), 2.58 (s, 3H). 5-669 (A) δ 7.88 (d, J = 8.0 Hz, 1H), 7.74(s, 1H), 7.64 (d, J = 8.0 Hz, 1H), 7.52 (d, J = 1.5 Hz, 2H), 7.44 (t, J= 1.5 Hz, 1H), 6.38 (bs, 1H), 6.02 (bs, 1H), 4.09 (d, J = 17.4 Hz, 1H),3.67 (d, J = 17.4 Hz, 1H). 5-670 (A) δ 7.66 (bs, 1H), 7.5-7.6 (m, 5H),5.74 (bs, 2H), 4.08 (d, J = 17.4 Hz, 1H), 3.68 (d, J = 17.4 Hz, 1H),2.53 (s, 3H). 5-672 (A) δ 8.09 (s, 2H), 7.97 (s, 1H), 7.5-7.6 (m, 3H),5.79 (bs, 2H), 4.21 (d, J = 17.4 Hz, 1H), 3.76 (d, J = 17.4 Hz, 1H),2.53 (s, 3H). 5-677 (A) δ 7.4-7.6 (m, 6H), 5.70 (bs, 2H), 4.09 (d, J =17.4 Hz, 1H), 3.70 (d, J = 17.4 Hz, 1H), 2.88 (q, J = 7.8 Hz, 2H), 1.26(t, J = 7.8 Hz, 3H). 5-679 (A) δ 7.35-8.25 (m, 6H), 6.97 (bs, 1H), 6.70(t, J = 72.3 Hz, 1H), 6.27 (bs, 1H), 4.10 (d, J = 17.1 Hz, 1H), 3.72 (d,J = 17.1 Hz, 1H). 5-680 (A) δ 7.45-8.0 (m, 6H), 6.80 (bs, 2H), 4.10 (d,J = 17.4 Hz, 1H), 3.20 (d, J = 17.4 Hz, 1H). 5-682 (A) δ 11.3 (s, 1H),7.4-8.85 (m, 8H), 4.15 (d, J = 17.4 Hz, 1H), 3.75 (d, J = 17.4 Hz, 1H),2.05 (s, 3H). 5-684 (A) δ 7.81 (s, 1H), 7.75 (s, 1H), 7.69 (s, 1H),7.5-7.55 (m, 2H), 7.43 (d, J = 8.1 Hz, 1H), 6.06 (t, J = 6.6 Hz, 1H),4.05-4.2 (m, 3H), 3.72 (d, J = 17.4 Hz, 1H), 2.46 (s, 3H). 5-685 (A) δ6.58 (d, J = 6.3 Hz, 2H), 7.5-7.55 (m, 2H), 7.43 (d, J = 8.1 Hz, 1H),6.05 (t, J = 6.6 Hz, 1H), 4.05-4.2 (m, 3H), 3.68 (d, J = 17.4 Hz, 1H),2.45 (s, 3H). 5-686 (A) δ 7.90 (dd, J = 6.3, 2.1 Hz, 1H), 7.75 (d, J =5.7 Hz, 1H), 7.5-7.55 (m, 2H), 7.43 (d, J = 8.1 Hz, 1H), 6.06 (t, J =6.6 Hz, 1H), 4.05-4.2 (m, 3H), 3.70 (d, J = 17.4 Hz, 1H), 2.44 (s, 3H).6-001 (A) δ 7.4-7.55 (m, 6H), 6.06 (bs, 1H), 5.39 (d, J = 28.6 Hz, 2H),4.24 (d, J = 6.0 Hz, 2H), 4.05 (d, J = 17.0 Hz, 1H), 3.67 (d, J = 17.3Hz, 1H), 2.49 (s, 3H). 6-003 (A) δ 7.45-7.55 (m, 4H), 7.43 (s, 1H), 7.23(d, J = 7.8 Hz, 1H), 4.09 (d, J = 17.1 Hz, 1H), 3.71 (d, J = 17.1 Hz,1H), 3.43 (bs, 2H), 3.10 (bs, 2H), 2.32 (s, 3H), 1.26 (t, J = 6.9 Hz,3H), 1.03 (t, J = 6.9 Hz, 3H). 6-005 (B) δ 7.98 (m, 1H), 7.2-7.6 (m,6H), 4.09 (d, J = 17.0 Hz, 1H), 3.18 (bs, 1H), 3.71 (d, J = 17.0 Hz,1H), 3.40 (bs, 1H), 2.43 and 2.33 (s, 3H), 2.12 and 1.66 (s, 3H), 1.23and 1.08 (bs, 3H). 6-006 (B) δ 7.2-7.6 (m, 6H), 4.05-4.15 (m, 1H),3.75-3.9 and 3.35-3.5 (m, 2H), 3.7 and 3.8 (m, 1H), 2.41 and 2.38 (s,3H), 2.23 and 1.80 (s, 3H), 2.00 and 1.77 (s, 3H), 1.25-1.3 and 1.05-1.1(m, 3H). 6-007 (B) δ 7.5-7.6 (m, 4H), 7.4-7.45 (m, 1H), 7.2-7.25 (m,1H), 3.2-4.7 (m, 4H), 4.10 (d, J = 17.0 Hz, 1H), 3.72 (d, J = 17.0 Hz,1H), 2.35 and 2.33 (s, 3H), 1.65-1.8 and 1.5-1.6 (m, 2H), 1.4-1.5 and1.1-1.25 (m, 2H), 1.0-1.05 and 0.75-0.85 (m, 3H). 6-008 (B) δ 7.6-7.65(m, 2H), 7.5-7.55 (m, 2H), 7.4-7.45 (m, 1H), 7.3-7.35 (m, 1H), 4.65 (bs,2H), 4.19 (bs, 2H), 4.09 (d, J = 17.0 Hz, 1H), 3.71 (d, J = 17.0 Hz,1H), 2.37 (s, 3H). 6-010 (B) δ 7.5-7.55 (m, 4H), 7.3-7.5 (m, 7H), 4.85(bs, 2H), 4.08 (d, J = 17.0 Hz, 1H), 3.69 (d, J = 17.0 Hz, 1H), 3.35(bs, 3H), 2.27 (s, 3H). 6-011 (B) δ 7.4-7.55 (m, 5H), 7.25-7.4 (m, 6H),4.90 (bs, 2H), 4.07 (d, J = 17.0 Hz, 1H), 3.68 (d, J = 17.0 Hz, 1H),2.40 (s, 3H), 1.88 (bs, 3H). 6-012 (B) δ 7.4-7.55 (m, 5H), 7.25-7.4 (m,6H), 4.43 (bs, 2H), 4.07 (d, J = 17.0 Hz, 1H), 3.78 (bs, 3H), 3.68 (d, J= 17.0 Hz, 1H), 2.38 (s, 3H). 6-013 (B) δ 7.5-7.6 (m, 4H), 7.4-7.45 (m,1H), 7.3-7.4 (m, 4H), 7.15-7.25 (m, 2H), 4.93 (bs, 2H), 4.08 (d, J =17.0 Hz, 1H), 3.69 (d, J = 17.0 Hz, 1H), 3.05 (bs, 3H), 2.28 (s, 3H).6-015 (A) δ 8.82 (s, 1H), 7.35-7.6 (m, 6H), 7.08 (s, 1H), 4.75-5.2 (m,2H), 4.56 (bs, 2H), 4.08 (d, J = 17.4 Hz, 1H), 3.79 (d, J = 17.4 Hz,1H), 2.36 and 2.29 (s, 3H). 6-016 (A) δ 8.80 and 8.77 (d, J = 7.8 Hz,1H), 7.45-7.55 (m, 4H), 7.3-7.45 (m, 3H), 4.85-5.2 (m, 1H), 4.2-4.7 (m,2H), 4.07 and 4.08 (d, J = 17.4 Hz, 1H), 3.75-4.0 (m, 1H), 3.69 (d, J =17.4 Hz, 1H), 2.31 and 2.36 (s, 3H), 2.25-2.3 (m, 1H). 6-017 (B) δ 8.72(s, 1H), 7.5-7.6 (m, 4H), 7.48 (s, 1H), 7.4-7.45 (m, 1H), 7.18 (s, 1H),5.03 (s, 2H), 4.07 (d, J = 17.0 Hz, 1H), 3.68 (d, J = 17.0 Hz, 1H), 2.41(s, 3H), 2.35 (s, 3H). 6-018 (A) δ 8.72 (s, 1H), 7.45-7.55 (m, 4H),7.4-7.45 (m, 1H), 7.31 (d, J = 7.8 Hz, 1H), 7.20 (s, 1H), 5.04 (s, 2H),4.07 (d, J = 17.4 Hz, 1H), 3.68 (d, J = 17.4 Hz, 1H), 2.75 (q, J = 7.2Hz, 2H), 2.34 (s, 3H), 1.12 (t, J = 7.2 Hz, 3H). 6-019 (B) δ 8.80 (s,1H), 7.55-7.6 (m, 4H), 7.42 (s, 1H), 7.25-7.3 (m, 2H), 5.26 (s, 2H),4.07 (d, J = 17.0 Hz, 1H), 3.68 (d, J = 17.0 Hz, 1H), 3.62 (s, 3H), 2.33(s, 3H). 6-021 (B) δ 8.5-8.6 (m, 1H), 7.65-7.75 (m, 1H), 7.4-7.6 (m,5H), 7.1-7.35 (m, 3H), 3.0-5.3 (m, 4H), 4.0-4.15 (m, 1H), 3.65-3.8 (m,1H), 2.37 and 2.34 (s, 3H), 1.25-1.35 and 1.0-1.1 (m, 3H). 6-022 (B) δ8.55-8.6 (m, 1H), 7.65-7.75 (m, 1H), 7.05-7.55 (m, 8H), 4.3-5.3 (m, 2H),4.0-4.15 (m, 1H), 2.9-4.1 (m, 2H), 3.65-3.75 (m, 1H), 2.37 and 2.32 (s,3H), 1.65-1.75 and 1.45-1.55 (m, 2H), 0.95-1.0 and 0.65-0.75 (m, 3H).6-023 (B) δ 8.55-8.6 and 8.45-8.5 (m, 1H), 7.4-7.7 (m, 7H), 7.25-7.35(m, 1H), 7.1-7.2 (m, 1H), 4.90 (d, J = 16.0 Hz, 1H), 4.76 (d, J = 16.0Hz, 1H), 4.0-4.15 (m, 1H), 3.6-3.85 (m, 2H), 2.42 and 2.34 (s, 3H), 1.23and 1.06 (bs, 6H). 6-024 (B) δ 8.5-8.6 (m, 1H), 7.05-7.7 (m, 9H), 4.83and 4.39 (s, 2H), 4.0-4.15 (m, 1H), 3.65-3.8 (m, 1H), 2.75-2.85 and2.65-2.7 (m, 1H), 2.36 and 2.33 (s, 3H), 0.75-0.9 and 0.45-0.6 (m, 4H).6-025 (B) δ 8.5-8.55 (m, 1H), 7.65-7.7 (m, 1H), 7.15-7.5 (m, 8H), 4.45and 4.16 (bs, 2H), 4.02 (d, J = 17.0 Hz, 1H), 3.63 (d, J = 17.0 Hz, 1H),2.38 (s, 3H), 1.54 (s, 9H). 6-026 (B) δ 8.55-8.6 (m, 1H), 7.2-7.75 (m,8H), 6.92 (d, J = 7.7 Hz, 1H), 3.7-5.25 (br, 4H), 4.1-4.15 (m, 1H),3.65-3.7 (m, 1H), 2.04 and 2.26 (s, 3H). 6-027 (A) δ 8.55 (bs, 1H),6.95-7.75 (m, 9H), 5.07 and 4.93 (bs, 2H), 4.53 and 4.48 (bs, 2H), 4.09and 4.05 (d, J = 17.1 Hz, 1H), 3.70 and 3.66 (d, J = 17.4 Hz, 1H), 3.47and 3.14 (s, 3H), 2.38 and 2.33 (s, 3H). 6-028 (B) δ 8.5-8.6 (m, 1H),7.6-7.75 (m, 1H), 7.05-7.55 (m, 8H), 3.25-5.2 (m, 8H), 3.37 and 3.17 (s,3H), 2.28 and 2.34 (s, 3H). 6-029 (A) δ 8.5-8.6 (m, 1H), 6.95-7.75 (m,9H), 4.98 (bs, 2H), 4.58 and 4.37 (bs, 2H), 4.09 and 4.05 (d, J = 17.2Hz, 1H), 3.70 and 3.67 (d, J = 17.2 Hz, 1H), 2.38 and 2.31 (s, 3H), 2.29and 1.99 (s, 3H). 6-030 (B) δ 8.5-8.65 (m, 1H), 7.15-7.8 (m, 8H),7.0-7.05 (m, 1H), 3.5-5.3 (m, 6H), 3.77 and 3.65 (s, 3H), 2.45 and 2.32(s, 3H). 6-031 (B) δ 8.5-8.65 (m, 1H), 7.2-7.8 (m, 8H), 6.9-7.0 (m, 1H),4.0-5.2 (m, 5H), 3.6-3.8 (m, 1H), 2.35 (s, 3H). 6-032 (B) δ 8.5-8.65 (m,1H), 7.0-7.8 (m, 9H), 5.8-6.0 and 5.55-5.75 (m, 1H), 3.6-5.55 (m, 8H),2.37 and 2.34 (s, 3H). 6-033 (B) δ 8.5-8.65 (m, 1H), 7.05-7.75 (m, 9H),3.5-5.3 (m, 6H), 2.37 (s, 3H), 2.28 (s, 1H). 6-034 (B) δ 8.45-8.5 (m,1H), 7.6-7.65 (m, 1H), 7.4-7.55 (m, 6H), 7.15-7.2 (m, 2H), 4.98 (s, 2H),4.06 (d, J = 17.0 Hz, 1H), 3.68 (d, J = 17.0 Hz, 1H), 2.41 (s, 3H), 2.39(s, 3H). 6-035 (A) δ 8.45-8.55 (m, 1H), 7.6-7.7 (m, 1H), 7.35-7.55 (m,6H), 7.1-7.25 (m, 2H), 4.99 (s, 2H), 4.06 (d, J = 19.0 Hz, 1H), 3.67 (d,J = 19.0 Hz, 1H), 2.74 (q, J = 8.2 Hz, 2H), 2.39 (s, 3H), 1.11 (t, J =8.2 Hz, 3H). 6-036 (A) δ 8.49 (d, J = 4.8 Hz, 1H), 7.63 (td, J = 7.8,1.8 Hz, 1H), 7.35-7.55 (m, 6H), 7.1-7.2 (m, 2H), 4.98 (s, 2H), 4.06 (d,J = 17.4 Hz, 1H), 3.67 (d, J = 17.4 Hz, 1H), 2.70 (t, J = 7.2 Hz, 2H),1.64 (hex, J = 7.2 Hz, 2H), 1.55 (s, 3H), 0.89 (t, J = 7.2 Hz, 3H).6-037 (A) δ 8.49 (d, J = 5.1 Hz, 1H), 7.63 (td, J = 7.8, 1.8 Hz, 1H),7.35-7.55 (m, 6H), 7.1-7.25 (m, 2H), 4.99 (s, 2H), 4.06 (d, J = 17.4 Hz,1H), 3.77 (d, J = 17.4 Hz, 1H), 3.1-3.3 (m, 1H), 2.42 (s, 3H), 1.13 (d,J = 6.6 Hz, 6H). 6-038 (A) δ 8.53 (d, J = 4.8 Hz, 1H), 7.64 (td, J =7.8, 1.8 Hz, 1H), 7.45-7.55 (m, 5H), 7.4-7.45 (m, 1H), 7.15-7.3 (m, 2H),5.16 (s, 2H), 4.08 (d, J = 17.4 Hz, 1H), 3.68 (d, J = 17.4 Hz, 1H), 2.45(s, 3H), 1.9-2.0 (m, 1H), 0.95-1.05 (m, 2H), 0.7-0.8 (m, 2H). 6-039 (A)δ 8.50 (d, J = 5.2 Hz, 1H), 7.55-7.65 (m, 1H), 7.4-7.55 (m, 6H), 7.1-7.2(m, 2H), 4.86 (s, 2H), 4.06 (d, J = 19.0 Hz, 1H), 3.68 (d, J = 19.0 Hz,1H), 2.44 (s, 3H), 1.34 (s, 9H). 6-041 (B) δ 8.5-8.55 (m, 1H), 7.6-7.7(m, 1H), 7.4-7.55 (m, 6H), 7.27 (s, 1H), 7.15-7.2 (m, 1H), 6.47 (dd, J =16.0, 10.0 Hz, 1H), 6.30 (d, J = 16.0 Hz, 1H), 5.62 (d, J = 10.0 Hz,1H), 5.10 (s, 2H), 4.07 (d, J = 17.0 Hz, 1H), 3.69 (d, J = 17.0 Hz, 1H),2.44 (s, 3H). 6-042 (A) δ 8.54 (d, J = 0.9 Hz, 1H), 8.09 (d, J = 7.6 Hz,1H), 7.15-7.75 (m, 13H), 5.32 (s, 2H), 3.95 (d, J = 19.0 Hz, 1H), 3.58(d, J = 19.0 Hz, 1H), 2.34 (s, 3H). 6-043 (A) δ 8.56 (d, J = 4.8 Hz,1H), 7.65-7.7 (m, 1H), 7.5-7.55 (m, 4H), 7.35-7.45 (m, 2H), 7.15-7.3 (m,2H), 5.21 (s, 2H), 4.09 (d, J = 17.4 Hz, 1H), 3.70 (d, J = 17.4 Hz, 1H),3.58 (s, 3H), 2.40 (s, 3H). 6-044 (A) δ 8.56 (d, J = 3.9 Hz, 1H), 7.65(td, J = 7.8, 1.8 Hz, 1H), 7.35-7.55 (m, 6H), 7.15-7.3 (m, 2H), 5.21 (s,2H), 4.09 (d, J = 17.4 Hz, 1H), 4.00 (q, J = 7.2 Hz, 2H), 3.69 (d, J =17.4 Hz, 1H), 2.41 (s, 3H), 0.92 (t, J = 7.2 Hz, 3H). 6-045 (A) δ 8.55(d, J = 4.8 Hz, 1H), 7.67 (td, J = 7.8, 1.8 Hz, 1H), 7.45-7.55 (m, 4H),7.35-7.45 (m, 2H), 7.15-7.3 (m, 2H), 5.20 (s, 2H), 4.7-4.85 (m, 1H),4.08 (d, J = 17.4 Hz, 1H), 3.69 (d, J = 17.4 Hz, 1H), 2.54 (s, 3H), 0.91(d, J = 6.3 Hz, 6H). 6-046 (B) δ 8.5-8.6 (m, 1H), 7.65-7.7 (m, 1H),7.5-7.55 (m, 4H), 7.4-7.45 (m, 2H), 7.25-7.3 (m, 1H), 7.15-7.2 (m, 1H),5.23 (s, 2H), 4.17 (d, J = 17.0 Hz, 1H), 3.75 (d, J = 6.8 Hz, 1H), 3.69(d, J = 17.0 Hz, 1H), 2.42 (s, 3H), 1.55-1.65 (m, 1H), 0.64 (d, J = 6.8Hz, 6H). 6-047 (B) δ 8.5-8.6 (m, 1H), 7.65-7.7 (m, 1H), 7.5-7.55 (m,4H), 7.4-7.45 (m, 2H), 7.25-7.3 (m, 1H), 7.15-7.25 (m, 1H), 5.23 (s,2H), 4.15-4.25 (m, 2H), 4.08 (d, J = 17.0 Hz, 1H), 3.70 (d, J = 17.0 Hz,1H), 3.3-3.4 (m, 2H), 2.42 (s, 3H). 6-048 (B) δ 8.55-8.6 (m, 1H),7.65-7.7 (m, 1H), 7.5-7.55 (m, 4H), 7.4-7.5 (m, 2H), 7.25-7.3 (m, 1H),7.15-7.25 (m, 1H), 5.23 (s, 2H), 4.05-4.15 (m, 3H), 3.69 (d, J = 17.0Hz, 1H), 3.2-3.25 (m, 2H), 3.15 (s, 3H), 2.49 (s, 3H). 6-049 (B) δ8.5-8.6 (m, 1H), 7.65-7.7 (m, 1H), 7.45-7.55 (m, 4H), 7.4-7.45 (m, 2H),7.25-7.3 (m, 1H), 7.15-7.2 (m, 1H), 5.45-5.6 (m, 1H), 5.23 (s, 2H),5.0-5.1 (m, 2H), 4.4-4.45 (m, 2H), 4.18 (d, J = 17.0 Hz, 1H), 3.69 (d, J= 17.0 Hz, 1H), 2.40 (s, 3H). 6-050 (B) δ 8.54 (d, J = 4.8 Hz, 1H),7.6-7.7 (m, 1H), 7.35-7.55 (m, 6H), 7.15-7.25 (m, 2H), 5.13 (s, 2H),4.07 (d, J = 17.0 Hz, 1H), 3.68 (d, J = 17.0 Hz, 1H), 2.40 (s, 3H), 2.27(s, 3H). 6-051 (B) δ 8.55-8.6 (m, 1H), 7.6-7.65 (m, 1H), 7.45-7.5 (m,5H), 7.35-7.4 (m, 1H), 7.2-7.25 (m, 1H), 7.0-7.05 (m, 1H), 4.96 (s, 2H),4.05 (d, J = 17.0 Hz, 1H), 3.67 (d, J = 17.0 Hz, 1H), 3.43 (s, 3H), 2.37(s, 3H). 6-053 (B) δ 8.65-8.7 (m, 1H), 7.65-7.8 (m, 2H), 7.5-7.55 (m,2H), 7.3-7.45 (m, 5H), 5.17 (s, 2H), 4.05 (d, J = 17.0 Hz, 1H), 3.67 (d,J = 17.0 Hz, 1H), 3.50 (s, 6H), 2.46 (s, 3H). 6-054 (B) δ 8.4-8.45 (m,1H), 7.8-7.85 (m, 1H), 7.2-7.6 (m, 7H), 4.2-5.3 (m, 2H), 4.05-4.15 (m,1H), 3.65-3.75 (m, 1H), 3.05-3.15 (m, 2H), 2.34 and 2.29 (s, 3H),1.25-1.3 and 1.0-1.1 (m, 3H). 6-055 (A) δ 8.6-8.65 (m, 2H), 7.5-7.55 (m,4H), 7.43 (s, 1H), 7.25-7.3 (m, 3H), 4.76 (s, 2H), 4.11 (d, J = 19.0 Hz,1H), 3.71 (d, J = 19.0 Hz, 1H), 2.45-2.5 (m, 1H), 2.34 (s, 3H), 1.2-1.3(m, 4H). 6-056 (A) δ 8.6-8.75 (m, 2H), 7.4-7.6 (m, 6H), 7.15-7.25 (m,1H), 5.12 (s, 2H), 4.06 (d, J = 17.0 Hz, 1H), 3.68 (d, J = 17.0 Hz, 1H),2.69 (q, J = 7.9 Hz, 2H), 2.43 (s, 3H), 1.11 (t, J = 7.9 Hz, 3H). 6-069(B) δ 7.8-7.9 (m, 2H), 7.67 (d, J = 7.6 Hz, 1H), 7.51 (bs, 2H), 7.4-7.45(m, 1H), 4.42 (s, 2H), 4.13 (d, J = 17.4 Hz, 1H), 3.77 (d, J = 17.4 Hz,1H), 3.22 (s, 3H). 6-070 (A) δ 8.55 (d, J = 4.4 Hz, 1H), 7.92 (d, J =7.8 Hz, 1H), 7.81 (s, 1H), 7.15-7.7 (m, 7H), 4.93 (s, 2H), 4.52 (s, 2H),4.13 (d, J = 17.0 Hz, 1H), 3.76 (d, J = 17.0 Hz, 1H). 6-073 (A) δ 8.55(d, J = 4.7 Hz, 1H), 8.37 (bs, 1H), 8.02 (d, J = 8.5 Hz, 1H), 7.91 (d, J= 8.5 Hz, 1H), 7.83 (bs, 1H), 7.69 (t, J = 7.7 Hz, 1H), 7.52 (bs, 2H),7.4-7.5 (m, 2H), 7.15-7.3 (m, 1H), 5.27 (s, 2H), 4.15 (d, J = 17.3 Hz,1H), 3.77 (d, J = 17.3 Hz, 1H). 6-074 (B) δ 7.5-7.7 (m, 4H), 7.43 (s,1H), 7.35-7.4 (m, 1H), 4.50 (q, J = 8.4 Hz, 2H), 4.16 (d, J = 17.0 Hz,1H), 3.75 (d, J = 17.0 Hz, 1H), 2.44 (s, 3H), 2.15 (s, 3H). 6-075 (B) δ7.7-7.8 (m, 3H), 7.55-7.65 (m, 2H), 7.35-7.4 (m, 1H), 4.50 (q, J = 8.6Hz, 2H), 4.10 (d, J = 17.0 Hz, 1H), 3.71 (d, J = 17.0 Hz, 1H), 2.44 (s,3H), 2.16 (s, 3H). 6-076 (B) δ 8.45-8.5 (m, 2H), 7.7-7.75 (m, 2H),7.6-7.65 (m, 1H), 7.69 (s, 1H), 7.4-7.45 (m, 2H), 7.15-7.2 (m, 2H), 4.97(s, 2H), 4.06 (d, J = 17.0 Hz, 1H), 3.68 (d, J = 17.0 Hz, 1H), 2.41 (s,3H), 2.40 (s, 3H). 6-077 (B) δ 7.5-7.6 (m, 4H), 7.43 (t, J = 1.8 Hz,1H), 7.23 (d, J = 7.9 Hz, 1H), 4.62 (q, J = 8.4 Hz, 2H), 4.08 (d, J =17.2 Hz, 1H), 3.70 (d, J = 17.2 Hz, 1H), 3.67 (s, 3H), 2.36 (s, 3H).6-078 (A) δ 8.79 and 8.75 (d, J = 1.8 Hz, 1H), 7.3-7.55 (m, 7H),4.85-5.2 (m, 2H), 4.53 and 4.50 (bs, 2H), 4.08 (d, J = 17.1 Hz, 1H),3.69 (d, J = 17.1 Hz, 1H), 3.47 and 3.14 (s, 3H), 2.36 and 2.25 (s, 3H).6-079 (A) δ 8.55 and 8.53 (d, J = 4.8 Hz, 1H), 7.69 and 7.59 (td, J =7.8, 1.8 Hz, 1H), 7.25-7.55 (m, 8H), 4.8-5.25 (m, 2H), 4.57 and 4.49(bs, 2H), 4.09 (d, J = 17.1 Hz, 1H), 3.70 (d, J = 17.1 Hz, 1H), 3.65 and3.27 (q, J = 6.9 Hz, 2H), 2.37 and 2.34 (s, 3H), 1.26 and 1.08 (t, J =6.9 Hz, 3H). 6-080 (B) δ 8.58 (ddd, J = 4.9, 1.8, 0.9 Hz, 1H), 7.70 (td,J = 7.7, 1.8 Hz, 1H), 7.35-7.55 (m, 7H), 7.18 (dd, J = 7.5, 4.9 Hz, 1H),5.98 (q, J = 7.1 Hz, 1H), 4.08 (d, J = 17.2 Hz, 1H), 3.70 (d, J = 17.2Hz, 1H), 3.42 (s, 3H), 2.43 (s, 3H), 1.90 (d, J = 7.0 Hz, 3H). 6-081 (A)δ 8.21 (d, J = 4.2 Hz, 1H), 7.3-7.6 (m, 7H), 6.80 (dd, J = 8.1, 4.2 Hz,1H), 6.60 (d, J = 8.7 Hz, 1H), 4.05 (d, J = 17.1 Hz, 1H), 3.66 (d, J =17.1 Hz, 1H), 3.34 (s, 3H), 2.45 (s, 3H), 2.42 (s, 3H). 6-082 (A) δ 8.22(d, J = 4.8 Hz, 1H), 7.4-7.65 (m, 7H), 6.78 (dd, J = 7.2, 4.8 Hz, 1H),6.63 (d, J = 8.4 Hz, 1H), 4.08 (d, J = 16.8 Hz, 1H), 3.70 (s, 3H), 3.69(d, J = 16.8 Hz, 1H), 3.40 (s, 3H), 2.46 (s, 3H). 6-083 (A) δ 8.42 (s,2H), 7.35-7.55 (m, 6H), 6.77 (t, J = 5.1 Hz, 1H), 4.06 (d, J = 18.1 Hz,1H), 3.67 (d, J = 18.1 Hz, 1H), 3.43 (s, 3H), 2.44 (s, 3H), 2.43 (s,3H). 6-084 (A) δ 8.46 (bs, 1H), 8.40 (bs, 1H), 7.45-7.6 (m, 5H), 7.43(s, 1H), 6.74 (t, J = 4.8 Hz, 1H), 4.09 (d, J = 17.4 Hz, 1H), 3.70 (d, J= 17.4 Hz, 1H), 3.69 (s, 3H), 3.53 (s, 3H), 2.46 (s, 3H). 6-085 (B) δ7.4-7.55 (m, 5H), 7.2-7.3 (m, 1H), 3.85-4.2 (m, 3H), 3.6-3.8 (m, 1H),2.5-2.65 (m, 2H), 2.32 and 2.30 (s, 3H), 2.1-2.2 (m, 2H). 6-086 (A) δ7.4-7.6 (m, 6H), 4.09 (d, J = 17.2 Hz, 1H), 3.71 (d, J = 17.2 Hz, 1H),2.89 (s, 4H), 2.57 (s, 3H). 6-089 (B) δ 7.45-7.6 (m, 4H), 7.4-7.45 (m,1H), 7.2-7.3 (m, 1H), 4.09 (d, J = 17.4 Hz, 1H), 3.71 (d, J = 17.4 Hz,1H), 3.13 (bs, 3H), 2.7-2.8 (m, 2H), 2.37 (bs, 3H), 1.15 (m, 3H). 6-092(B) δ 7.45-7.55 (m, 4H), 7.4-7.45 (m, 1H), 7.33 (d, J = 8.0 Hz, 1H),5.10 (s, 2H), 4.50 (s, 2H), 4.09 (d, J = 17.2 Hz, 1H), 3.6-3.75 (m, 3H),3.27 (q, J = 6.8 Hz, 2H), 2.36 (s, 3H), 1.25 (t, J = 7.0 Hz, 3H), 1.10(t, J = 7.0 Hz, 3H). 6-093 (A) δ 7.5-7.7 (m, 4H), 7.44 (t, J = 2.0 Hz,1H), 7.35 (d, J = 7.6 Hz, 1H), 5.03 (s, 2H), 4.11 (d, J = 17.4 Hz, 1H),3.70 (d, J = 17.4 Hz, 1H), 3.50 (q, J = 7.0 Hz, 2H), 2.48 (s, 3H), 2.40(s, 3H), 1.15 (t, J = 7.0 Hz, 3H). 6-094 (A) δ 7.5-7.6 (m, 4H), 7.44 (t,J = 1.8 Hz, 1H), 7.2-7.3 (m, 1H), 5.14 and 4.62 (s, 2H), 4.05-4.15 (m,2H), 3.6-3.75 (m, 2H), 3.20 and 2.87 (s, 3H), 2.33 and 2.35 (s, 3H).6-095 (B) δ 7.3-7.6 (m, 6H), 5.15 (s, 2H), 3.95-4.2 (m, 3H), 3.71 (d, J= 17.4 Hz, 1H), 2.48 (s, 3H), 2.40 (s, 3H). 6-096 (B) δ 7.45-7.55 (m,4H), 7.43 (t, J = 1.8 Hz, 1H), 7.24 (d, J = 8.1 Hz, 1H), 4.12 (t, J =5.5 Hz, 2H), 4.09 (d, J = 17.2 Hz, 1H), 3.71 (d, J = 17.2 Hz, 1H), 3.66(t, J = 5.5 Hz, 2H), 3.61 (s, 3H), 3.37 (s, 3H), 2.36 (s, 3H). 6-097 (A)δ 7.4-7.55 (m, 5H), 7.2-7.3 (m, 1H), 5.18 and 4.87 (t, J = 4.6 Hz, 1H),3.65-4.2 (m, 8H), 3.20 and 2.89 (s, 3H), 2.34 and 2.32 (s, 3H). 6-098(A) δ 7.5-7.6 (m, 4H), 7.44 (t, J = 1.8 Hz, 1H), 7.37 (d, J = 7.8 Hz,1H), 5.12 (t, J = 4.6 Hz, 1H), 4.09 (d, J = 17.4 Hz, 1H), 3.8-3.95 (m,6H), 3.70 (d, J = 17.4 Hz, 1H), 2.43 (s, 3H), 2.33 (s, 3H). 6-099 (A) δ7.45-7.55 (m, 4H), 7.43 (t, J = 1.8 Hz, 1H), 7.25-7.3 (m, 1H), 5.32 (t,J = 4.6 Hz, 1H), 3.9-4.15 (m, 7H), 3.69 (d, J = 17.4 Hz, 1H), 3.62 (s,3H), 2.38 (s, 3H). 6-100 (A) δ 7.4-7.65 (m, 6H), 5.72 (dd, J = 7.2, 5.7Hz, 1H), 4.10 (d, J = 17.1 Hz, 1H), 4.0-4.15 (m, 1H), 3.75-3.85 (m, 1H),3.71 (d, J = 17.1 Hz, 1H), 2.49 (s, 3H), 2.3-2.45 (m, 1H), 2.22 (s, 3H),2.1-2.25 (m, 2H), 1.8-1.95 (m, 1H). 6-101 (A) δ 7.35-7.6 (m, 5H),6.6-7.3 (m, 2H), 3.65-4.45 (m, 7H), 3.13 and 2.82 (d, J = 7.8 Hz, 3H),2.3-2.35 (m, 3H). 6-102 (A) δ 6.6-7.6 (m, 7H), 4.35-4.45 (m, 2H),3.65-4.15 (m, 5H), 2.3-2.45 (m, 6H). 6-103 (A) δ 6.65-7.55 (m, 7H),4.6-4.75 (m, 2H), 3.6-4.15 (m, 8H), 2.37 and 2.35 (s, 3H). 6-105 (B) δ7.45-7.55 (m, 4H), 7.43 (t, J = 1.8 Hz, 1H), 7.37 (d, J = 8.8 Hz, 2H),7.14 (d, J = 8.1 Hz, 1H), 6.87 (d, J = 8.8 Hz, 2H), 5.00 (s, 2H), 4.08(d, J = 17.2 Hz, 1H), 3.81 (s, 3H), 3.68 (d, J = 17.2 Hz, 1H), 3.58 (s,3H), 2.29 (s, 3H). 6-106 (B) δ 8.22 (d, J = 8.7 Hz, 2H), 7.59 (d, J =8.7 Hz, 2H), 7.45-7.55 (m, 4H), 7.43 (t, J = 1.8 Hz, 1H), 7.18 (d, J =7.9 Hz, 1H), 5.15 (s, 2H), 4.08 (d, J = 17.2 Hz, 1H), 3.70 (d, J = 17.2Hz, 1H), 3.58 (s, 3H), 2.16 (s, 3H). 6-107 (B) δ 7.3-7.6 (m, 14H), 7.19(d, J = 8.1 Hz, 1H), 5.11 (s, 2H), 4.07 (d, J = 17.2 Hz, 1H), 3.68 (d, J= 17.2 Hz, 1H), 3.60 (s, 3H), 2.37 (s, 3H). 6-108 (A) δ 7.81 (bs, 1H),7.4-7.55 (m, 5H), 7.2-7.3 (m, 1H), 6.56 (s, 1H), 6.13 (s, 2H), 4.07 (d,J = 17.3 Hz, 1H), 3.68 (d, J = 17.3 Hz, 1H), 2.28 (s, 3H), 1.23 (s, 9H).6-109 (B) δ 8.08 (dt, J = 7.5, 0.9 Hz, 1H), 7.89 (dt, J = 8.4, 0.9 Hz,1H), 7.4-7.6 (m, 7H), 7.14 (d, J = 8.1 Hz, 1H), 6.72 (s, 2H), 4.06 (d, J= 17.2 Hz, 1H), 3.69 (s, 3H), 3.68 (d, J = 17.2 Hz, 1H), 2.25 (s, 3H).6-111 (A) δ 8.56 (d, J = 4.2 Hz, 1H), 6.7-7.85 (m, 13H), 5.21 (s, 2H),4.00 (d, J = 17.4 Hz, 1H), 3.60 (d, J = 17.4 Hz, 1H), 2.40 (s, 3H).6-112 (A) δ 8.72 (d, J = 4.8 Hz, 2H), 7.4-7.6 (m, 6H), 7.22 (t, J = 4.8Hz, 1H), 5.33 (s, 2H), 4.10 (d, J = 17.1 Hz, 1H), 3.71 (d, J = 17.1 Hz,1H), 3.58 (s, 3H), 2.44 (s, 3H). 6-113 (B) δ 7.82 (t, J = 6.0 Hz, 1H),7.5-7.6 (m, 4H), 7.43 (bs, 1H), 7.2-7.3 (m, 1H), 4.8-4.85 (m, 1H),3.65-4.15 (m, 4H), 3.15-3.25 (m, 2H), 2.5-2.6 (m, 1H), 2.34 (s, 3H),1.85-2.1 (m, 3H). 6-114 (A) δ 7.5-7.6 (m, 4H), 7.43 (t, J = 2.0 Hz, 1H),7.25-7.35 (m, 1H), 5.19 (s, 1H), 4.59 (s, 1H), 4.0-4.2 (m, 3H), 3.65-3.8(m, 2H), 3.27 (t, J = 6.4 Hz, 1H), 2.39 (bs, 3H). 6-115 (A) δ 7.4-7.6(m, 5H), 7.25-7.35 (m, 1H), 4.77 (s, 1H), 4.0-4.2 (m, 3H), 3.70 (d, J =17.4 Hz, 1H), 3.45 (t, J = 6.4 Hz, 1H), 3.13 (t, J = 6.4 Hz, 1H), 2.97(t, J = 6.4 Hz, 1H), 2.36 (m, 3H). 6-119 (A) δ 7.4-7.55 (m, 6H), 4.08(d, J = 17.4 Hz, 1H), 3.8-3.85 (m, 2H), 3.69 (d, J = 17.4 Hz, 1H),3.2-3.25 (m, 2H), 2.45-2.5 (m, 2H), 2.2-2.35 (m, 8H). 6-120 (B) δ7.45-7.55 (m, 4H), 7.43 (t, J = 1.8 Hz, 1H), 7.30 (d, J = 7.9 Hz, 1H),4.08 (d, J = 17.2 Hz, 1H), 3.89 (s, 3H), 3.82 (s, 3H), 3.69 (d, J = 17.2Hz, 1H), 2.38 (s, 3H). 6-121 (B) δ 7.45-7.55 (m, 4H), 7.43 (t, J = 1.8Hz, 1H), 7.21 (d, J = 7.9 Hz, 1H), 4.09 (d, J = 17.2 Hz, 1H), 3.77 (s,3H), 3.70 (d, J = 17.2 Hz, 1H), 2.84 (s, 6H), 2.40 (s, 3H). 6-122 (B) δ8.0-8.15 (m, 1H), 7.4-7.6 (m, 5H), 4.11 (d, J = 17.4 Hz, 1H), 3.72 (d, J= 17.4 Hz, 1H), 2.68 (s, 3H), 2.33 (s, 6H). 6-123 (B) δ 7.45-7.55 (m,4H), 7.43 (t, J = 1.8 Hz, 1H), 7.31 (d, J = 7.9 Hz, 1H), 4.8-4.9 (m,1H), 4.76 (ddd, J = 47.6, 11.0, 2.4 Hz, 1H), 4.58 (ddd, J = 46.0, 11.0,2.7 Hz, 1H), 4.28 (dd, J = 11.2, 10.0 Hz, 1H), 4.18 (dd, J = 11.2, 5.5Hz, 1H), 4.08 (d, J = 17.2 Hz, 1H), 3.70 (d, J = 17.2 Hz, 1H), 2.35 (s,3H). 6-124 (B) δ 7.5-7.6 (m, 4H), 7.43 (t, J = 1.8 Hz, 1H), 7.34 (d, J =8.6 Hz, 1H), 4.09 (d, J = 17.2 Hz, 1H), 3.75 (s, 3H), 3.70 (d, J = 17.2Hz, 1H), 3.14 (bs, 3H), 3.07 (bs, 3H), 2.44 (s, 3H). 6-125 (B) δ 9.12(t, J = 7.3 Hz, 1H), 7.5-7.6 (m, 4H), 7.43 (t, J = 1.8 Hz, 1H), 7.23 (d,J = 8.2 Hz, 1H), 4.07 (d, J = 17.2 Hz, 1H), 3.68 (d, J = 17.2 Hz, 1H),3.39 (tq, J = 7.3, 7.1 Hz, 2H), 3.01 (s, 3H), 2.37 (s, 3H), 1.24 (t, J =7.1 Hz, 3H). 6-126 (B) δ 9.65 (t, J = 6.2 Hz, 1H), 7.15-7.65 (m, 4H),7.44 (t, J = 1.8 Hz, 1H), 7.29 (d, J = 7.9 Hz, 1H), 4.09 (d, J = 17.2Hz, 1H), 3.95-4.1 (m, 2H), 3.71 (d, J = 17.2 Hz, 1H), 3.07 (s, 3H), 2.36(s, 3H). 6-130 (A) δ 7.2-7.7 (m, 6H), 6.15 (s, 1H), 5.15-5.35 (m, 1H),4.5-4.8 (m, 1H), 4.09 (d, J = 17.4 Hz, 1H), 3.6-4.3 (m, 3H), 3.48 and3.03 (s, 3H), 2.36 and 2.34 (s, 3H), 1.7-2.45 (m, 4H). 6-131 (A) δ7.35-7.6 (m, 6H), 5.65-5.75 (m, 1H), 4.05-4.2 (m, 1H), 4.08 (d, J = 17.4Hz, 1H), 3.7-3.85 (m, 1H), 3.70 (d, J = 17.4 Hz, 1H), 2.51 (q, J = 6.0Hz, 2H), 2.49 (s, 3H), 1.6-2.6 (m, 4H), 1.08 (t, J = 6.0 Hz, 3H). 6-132(A) δ 7.5-7.6 (m, 4H), 7.4-7.45 (m, 2H), 5.78 (t, J = 6.3 Hz, 1H),4.05-4.15 (m, 2H), 3.75-3.85 (m, 1H), 3.71 (d, J = 17.4 Hz, 1H), 2.7-2.9(m, 1H), 2.50 (s, 3H), 2.25-2.4 (m, 1H), 2.1-2.25 (m, 2H), 1.8-1.95 (m,1H), 1.06 and 1.08 (d, J = 6.0 Hz, 6H). 7-002 (A) δ 7.87 (bs, 1H), 7.78(d, J = 8.1 Hz, 2H), 7.65 (d, J = 8.1 Hz, 2H), 7.50 (bs, 2H), 7.43 (bs,1H), 4.55-4.7 (m, 2H), 4.09 (d, J = 17.4 Hz, 1H), 3.71 (d, J = 17.4 Hz,1H). 7-003 (A) δ 8.85 (s, 1H), 8.49 (bs, 1H), 7.86 (d, J = 8.4 Hz, 2H),7.67 (d, J = 8.7 Hz, 2H), 7.51 (bs, 2H), 7.43 (d, J = 1.8 Hz, 1H), 7.40(s, 1H), 5.13 (d, J = 4.8 Hz, 2H), 4.06 (d, J = 17.4 Hz, 1H), 3.67 (d, J= 17.1 Hz, 1H). 7-008 (A) δ 8.79 (s, 1H), 8.14 (bs, 1H), 7.35-7.5 (m,7H), 5.11 (d, J = 5.0 Hz, 2H), 4.06 (d, J = 17.4 Hz, 1H), 3.67 (d, J =17.1 Hz, 1H), 2.37 (s, 3H). 7-009 (A) δ 9.06 (bs, 1H), 8.50 (d, J = 4.5Hz, 1H), 7.75 (t, J = 7.2 Hz, 1H), 7.2-7.6 (m, 8H), 5.04 (d, J = 4.2 Hz,2H), 4.08 (d, J = 17.4 Hz, 1H), 3.70 (d, J = 17.4 Hz, 1H), 2.44 (s, 3H).8-001 (A) δ 8.40 (d, J = 8.2 Hz, 2H), 7.74 (d, J = 8.2 Hz, 2H), 7.53 (s,2H), 7.43 (s, 1H), 7.04 (d, J = 4.7 Hz, 1H), 6.74 (d, J = 4.7 Hz, 1H),4.13 (d, J = 17.3 Hz, 1H), 3.89 (s, 3H), 3.74 (d, J = 17.3 Hz, 1H).8-002 (A) δ 8.22 (d, J = 8.0 Hz, 2H), 7.56 (s, 1H), 7.53 (s, 2H), 7.43(s, 1H), 7.03 (d, J = 4.7 Hz, 1H), 6.72 (d, J = 4.7 Hz, 1H), 4.12 (d, J= 17.3 Hz, 1H), 3.84 (s, 3H), 3.72 (d, J = 17.3 Hz, 1H), 2.74 (s, 3H).8-003 (A) δ 8.19 (d, J = 8.1 Hz, 1H), 7.5-7.6 (m, 4H), 7.43 (s, 1H),7.04 (d, J = 4.8 Hz, 1H), 6.71 (d, J = 4.8 Hz, 1H), 4.23 (t, J = 7.2 Hz,2H), 4.12 (d, J = 17.1 Hz, 1H), 3.72 (d, J = 17.1 Hz, 1H), 2.73 (s, 3H),1.91 (hex, J = 7.2 Hz, 2H), 0.99 (t, J = 7.2 Hz, 3H). 8-004 (A) δ 8.17(d, J = 8.1 Hz, 1H), 7.45-7.65 (m, 4H), 7.41 (s, 1H), 7.36 (t, J = 4.2Hz, 1H), 4.12 (d, J = 17.4 Hz, 1H), 3.79 (s, 3H), 3.74 (d, J = 17.4 Hz,1H), 3.17 (d, J = 4.2 Hz, 2H), 2.69 (s, 3H). 8-005 (A) δ 8.50 (s, 1H),7.95 (d, J = 7.8 Hz, 1H), 7.68 (d, J = 6.6 Hz, 1H), 7.4-7.6 (m, 5H),6.32 (dd, J = 6.6, 4.2 Hz, 1H), 4.10 (d, J = 17.4 Hz, 1H), 3.71 (d, J =17.4 Hz, 1H), 3.67 (s, 3H), 2.68 (s, 3H). 8-006 (A) δ 8.97 (s, 1H),7.3-7.7 (m, 6H), 4.12 (d, J = 17.4 Hz, 1H), 3.73 (d, J = 17.4 Hz, 1H),3.62 (s, 3H), 2.36 (s, 3H). 8-007 (A) δ 8.58 (d, J = 9.9 Hz, 1H), 8.08(d, J = 7.8 Hz, 1H), 7.4-7.6 (m, 5H), 7.30 (d, J = 9.9 Hz, 1H), 4.11 (d,J = 17.1 Hz, 1H), 4.00 (s, 3H), 3.72 (d, J = 17.1 Hz, 1H), 2.67 (s, 3H).9-003 (B) δ 8.75 (d, J = 1.2 Hz, 1H), 8.7-8.75 (m, 1H), 8.14 (t, J = 1.8Hz, 1H), 7.5-7.6 (m, 2H), 7.45 (d, J = 8.6 Hz, 1H), 6.0-6.05 (m, 1H),4.05-4.2 (m, 3H), 3.74 (d, J = 17.2 Hz, 1H), 2.48 (s, 3H). 9-008 (A) δ7.97 (s, 1H), 7.45-7.55 (m, 2H), 7.35-7.4 (m, 1H), 6.44 (t, J = 6.3 Hz,1H), 4.40 (d, J = 17.6 Hz, 1H), 4.0-4.15 (m, 3H), 2.42 (s, 3H). 9-009(A) δ 8.51 (dd, J = 5.1, 0.9 Hz, 1H), 7.96 (s, 1H), 7.70 (td, J = 7.5,1.5 Hz, 1H), 7.5-7.6 (m, 3H), 7.3-7.4 (m, 2H), 7.15-7.25 (m, 1H), 4.74(d, J = 4.8 Hz, 2H), 4.40 (d, J = 17.6 Hz, 1H), 4.09 (d, J = 17.6 Hz,1H), 2.50 (s, 3H). 9-010 (B) δ 7.45-7.55 (m, 2H), 7.40 (d, J = 7.9 Hz,1H), 7.04 (d, J = 4.0 Hz, 1H), 6.89 (d, J = 4.0 Hz, 1H), 6.25 (bs, 1H),4.05-4.15 (m, 2H), 4.03 (d, J = 17.2 Hz, 1H), 3.74 (d, J = 17.2 Hz, 1H),2.43 (s, 3H). 9-011 (B) δ 8.5-8.55 (m, 1H), 7.70 (td, J = 7.5, 1.8 Hz,1H), 7.45-7.65 (m, 3H), 7.43 (t, J = 5.1 Hz, 1H), 7.34 (d, J = 7.9 Hz,1H), 7.15-7.25 (m, 1H), 7.04 (d, J = 3.8 Hz, 1H), 6.88 (d, J = 4.0 Hz,1H), 4.73 (d, J = 5.0 Hz, 2H), 4.04 (d, J = 17.2 Hz, 1H), 3.74 (d, J =17.2 Hz, 1H), 2.48 (s, 3H). 10-001  (A) δ 8.87 (d, J = 2.1 Hz, 1H),8.25-8.3 (m, 2H), 8.14 (dd, J = 8.1, 2.1 Hz, 1H), 7.51 (bs, 2H), 7.45(d, J = 1.8 Hz, 1H), 4.05-4.2 (m, 3H), 3.75 (d, J = 17.4 Hz, 1H).10-002  (A) δ 8.94 (bs, 1H), 8.88 (bs, 1H), 8.61 (d, J = 5.1 Hz, 1H),8.30 (d, J = 7.8 Hz, 1H), 8.12 (dd, J = 8.1, 2.1 Hz, 1H), 7.68 (td, J =7.8, 1.8 Hz, 1H), 7.51 (bs, 2H), 7.45 (t, J = 1.8 Hz, 1H), 7.34 (d, J =7.8 Hz, 1H), 7.2-7.25 (m, 1H), 4.80 (d, J = 5.4 Hz, 2H), 4.12 (d, J =17.4 Hz, 1H), 3.74 (d, J = 17.4 Hz, 1H). 10-003  (A) δ 8.53 (d, J = 1.8Hz, 1H), 8.48 (d, J = 8.4 Hz, 1H), 7.74 (dd, J = 8.4, 1.8 Hz, 1H), 7.47(bs, 3H), 4.0-4.2 (m, 2H), 4.05 (d, J = 17.4 Hz, 1H), 3.68 (d, J = 17.4Hz, 1H). 10-004  (A) δ 9.01 (s, 1H), 8.17 (d, J = 8.4 Hz, 1H), 8.10 (d,J = 8.4 Hz, 1H), 7.51 (s, 2H), 7.43 (s, 1H), 6.77 (t, J = 6.3 Hz, 1H),4.26 (d, J = 18.3 Hz, 1H), 4.05-4.25 (m, 2H), 3.89 (d, J = 18.3 Hz, 1H).10-005  (A) δ 9.09 (s, 1H), 8.57 (d, J = 5.1 Hz, 1H), 8.24 (d, J = 8.4Hz, 1H), 8.12 (d, J = 8.4 Hz, 1H), 7.86 (bs, 1H), 7.65-7.75 (m, 1H),7.52 (s, 2H), 7.43 (s, 1H), 7.2-7.35 (m, 2H), 4.78 (d, J = 4.2 Hz, 2H),4.28 (d, J = 18.3 Hz, 1H), 3.90 (d, J = 18.3 Hz, 1H). 11-034  (A) δ 7.96(t, J = 7.0 Hz, 1H), 7.88 (dd, J = 8.2, 1.6 Hz, 1H), 7.81 (dd, J = 11.8,1.4 Hz, 1H), 7.51 (bs, 2H), 7.4-7.45 (m, 1H), 4.20 (dd, J = 18.2, 1.4Hz, 1H), 3.82 (d, J = 18.2 Hz, 1H). 11-038  (A) δ 7.89 (d, J = 8.1 Hz,1H), 7.72 (s, 1H), 7.64 (d, J = 8.1 Hz, 1H), 7.50 (s, 2H), 7.43 (s, 1H),4.09 (d, J = 17.1 Hz, 1H), 3.95 (s, 3H), 3.71 (d, J = 17.1 Hz, 1H).11-056  (A) δ 8.64 (d, J = 4.5 Hz, 1H), 8.06 (d, J = 8.4 Hz, 1H), 7.75(td, J = 7.7, 1.1 Hz, 1H), 7.5-7.6 (m, 4H), 7.35-7.45 (m, 2H), 7.28 (t,J = 6.2 Hz, 1H), 5.48 (s, 2H), 4.11 (d, J = 17.1 Hz, 1H), 3.72 (d, J =17.1 Hz, 1H), 2.65 (s, 3H). 11-057  (B) δ 8.4-8.45 (m, 1H), 7.75 (s,1H), 7.5-7.65 (m, 5H), 7.44 (s, 1H), 6.55 (s, 1H), 4.12 (d, J = 17.0 Hz,1H), 3.73 (d, J = 17.0 Hz, 1H), 2.37 (s, 3H). 11-059  (A) δ 7.90 (d, J =8.4 Hz, 1H), 7.4-7.7 (m, 5H), 4.11 (d, J = 17.4 Hz, 1H), 3.91 (s, 3H),3.72 (d, J = 17.4 Hz, 1H), 3.50 (q, J = 7.5 Hz, 2H), 1.25 (t, J = 7.5Hz, 3H). 11-060  (A) δ 8.02 (d, J = 6.3 Hz, 1H), 7.75 (s, 1H), 7.67 (d,J = 6.3 Hz, 1H), 7.51 (s, 2H), 7.43 (s, 1H), 4.95 (s, 2H), 4.12 (d, J =17.4 Hz, 1H), 3.97 (s, 3H), 3.74 (d, J = 17.4 Hz, 1H). 11-062  (B) δ8.07 (t, J = 0.8 Hz, 1H), 7.99 (ddd, J = 8.0, 1.6, 0.4 Hz, 1H), 7.93(dd, J = 7.4, 0.6 Hz, 1H), 7.48-7.52 (m, 2H), 7.46 (t, J = 1.4 Hz, 1H),4.11 (d, J = 16.8 Hz, 1H), 3.74 (dd, J = 17.4, 1.0 Hz, 1H). 11-063  (B)δ 8.00 (s, 1H), 7.93 (d, J = 8.1 Hz, 1H), 7.87 (d, J = 8.1 Hz, 1H), 7.51(s, 2H), 7.4-7.5 (m, 1H), 4.12 (d, J = 16.7 Hz, 1H), 3.96 (s, 3H), 3.74(d, J = 16.7 Hz, 1H). 11-071  (B) δ 8.03 (d, J = 8.0 Hz, 1H), 7.6-7.7(m, 2H), 7.51 (s, 2H), 7.4-7.5 (m, 1H), 4.09 (d, J = 17.2 Hz, 1H), 3.95(s, 3H), 3.70 (d, J = 17.2z, 1H). 11-073  (A) δ 7.95-8.05 (m, 1H),7.4-7.5 (m, 2H), 7.2-7.35 (m, 3H), 4.06 (d, J = 17.1 Hz, 1H), 3.95 (s,3H), 3.70 (d, J = 17.1 Hz, 1H), 2.52 (s, 3H). 11-092  (A) δ 7.94 (d, J =8.8 Hz, 1H), 7.4-7.6 (m, 5H), 4.37 (q, J = 7.1 Hz, 2H), 4.15 (d, J =17.3 Hz, 1H), 3.73 (d, J = 17.3 Hz, 1H), 2.62 (s, 3H), 1.40 (t, J = 7.1Hz, 3H). 11-095  (A) δ 7.94 (d, J = 8.8 Hz, 1H), 7.5-7.8 (m, 5H), 4.37(q, J = 7.1 Hz, 2H), 4.09 (d, J = 17.3 Hz, 1H), 3.70 (d, J = 17.3 Hz,1H), 2.62 (s, 3H), 1.40 (t, J = 7.1 Hz, 3H). 11-102  (A) δ 7.85-7.95 (m,1H), 7.35-7.6 (m, 5H), 6.91 (s, 1H), 4.05 (d, J = 17.4 Hz, 1H), 3.67 (d,J = 17.4 Hz, 1H). 11-105  (A) δ 8.06 (d, J = 8.4 Hz, 1H), 7.68 (dd, J =8.4, 1.8 Hz, 1H), 7.62 (d, J = 1.8 Hz, 1H), 7.50 (d, J = 1.5 Hz, 2H),7.43 (t, J = 1.5 Hz, 1H), 7.08 (s, 1H), 4.05 (d, J = 17.4 Hz, 1H), 3.67(d, J = 17.4 Hz, 1H). 11-107  (A) δ 7.68 (d, J = 1.8 Hz, 1H), 7.58 (dd,J = 8.1, 1.8 Hz, 1H), 7.45-7.55 (m, 3H), 7.43 (t, J = 1.8 Hz, 1H), 5.22(s, 2H), 4.06 (d, J = 17.4 Hz, 1H), 3.68 (d, J = 17.4 Hz, 1H), 2.15 (s,3H). 11-112  (A) δ 8.08 (d, J = 8.4 Hz, 1H), 7.79 (d, J = 1.8 Hz, 1H),7.73 (d, J = 8.4 Hz, 1H), 7.49 (d, J = 1.5 Hz, 2H), 7.44 (t, J = 1.5 Hz,1H), 7.04 (s, 1H), 4.06 (d, J = 17.4 Hz, 1H), 3.67 (d, J = 17.4 Hz, 1H).11-113  (A) δ 7.84 (s, 1H), 7.55-7.7 (m, 2H), 7.50 (d, J = 1.5 Hz, 2H),7.43 (t, J = 1.5 Hz, 1H), 4.77 (s, 2H), 4.07 (d, J = 17.4 Hz, 1H), 3.67(d, J = 17.4 Hz, 1H). 11-114  (A) δ 7.86 (s, 1H), 7.63 (d, J = 8.1 Hz,1H), 7.4-7.55 (m, 4H), 4.20 (s, 2H), 4.07 (d, J = 17.4 Hz, 1H), 3.67 (d,J = 17.4 Hz, 1H), 2.17 (s, 3H). 11-116  (A) δ 10.07 (s, 1H), 8.23 (s,1H), 7.91 (d, J = 8.4 Hz, 1H), 7.77 (d, J = 8.4 Hz, 1H), 7.50 (s, 2H),7.44 (s, 1H), 4.09 (d, J = 17.4 Hz, 1H), 3.70 (d, J = 17.4 Hz, 1H).11-118  (A) δ 7.5-7.55 (m, 3H), 7.48 (dd, J = 8.1, 1.8 Hz, 1H), 7.42 (t,J = 1.8 Hz, 1H), 7.38 (d, J = 8.1 Hz, 1H), 4.60 (s, 2H), 4.07 (d, J =17.4 Hz, 1H), 3.67 (d, J = 17.4 Hz, 1H), 2.45 (s, 3H). 11-119  (A) δ7.45-7.55 (m, 3H), 7.47 (s, 2H), 7.42 (s, 1H), 4.74 (s, 2H), 4.09 (d, J= 17.4 Hz, 1H), 3.70 (d, J = 17.4 Hz, 1H), 2.36 (s, 3H). 11-122  (A) δ9.35 (s, 1H), 7.4-7.45 (m, 5H), 7.2-7.3 (m, 1H), 4.39 (q, J = 7.1 Hz,2H), 4.21 (d, J = 17.3 Hz, 1H), 3.83 (d, J = 17.3 Hz, 1H), 1.40 (t, J =7.1 Hz, 3H). 11-125  (A) δ 7.45-8.05 (m, 6H), 6.66 (t, J = 72.3 Hz, 1H),4.08 (d, J = 17.4 Hz, 1H), 3.71 (d, J = 17.4 Hz, 1H). 11-126  (A) δ6.7-7.5 (m, 6H), 6.50 (t, J = 74.1 Hz, 1H), 4.23 (bs, 2H), 4.02 (d, J =17.4 Hz, 1H), 3.63 (d, J = 17.4 Hz, 1H). 11-127  (A) δ 7.2-7.95 (m, 6H),6.57 (t, J = 73.2 Hz, 1H), 4.05 (d, J = 17.4 Hz, 1H), 3.66 (d, J = 17.4Hz, 1H). 11-129  (A) δ 7.95 (q, J = 8.7 Hz, 1H), 7.66 (s, 1H), 7.5-7.6(m, 4H), 4.37 (q, J = 7.2 Hz, 2H), 4.10 (d, J = 17.4 Hz, 1H), 3.71 (d, J= 17.4 Hz, 1H), 2.62 (s, 3H), 1.40 (t, J = 7.2 Hz, 3H). 11-130  (A) δ8.09 (s, 2H), 7.95-8.0 (m, 2H), 7.5-7.6 (m, 2H), 4.38 (q, J = 7.2 Hz,2H), 4.21 (d, J = 17.4 Hz, 1H), 3.76 (d, J = 17.4 Hz, 1H), 2.63 (s, 3H),1.41 (t, J = 7.2 Hz, 3H). 14-004  (A) δ 7.40 (s, 1H), 7.35 (s, 2H), 5.99(s, 1H), 5.65 (s, 1H). 14-005  (B) δ 7.2-7.45 (m, 3H), 6.10 (s, 1H),5.92 (s, 1H). 14-006  (A) δ 7.40 (s, 2H), 7.33 (s, 1H), 5.63 (s, 1H),5.45 (s, 1H), 4.47 (s, 2H), 3.84 (q, J = 8.8 Hz, 2H). 14-007  (B) δ7.3-7.4 (m, 3H), 5.22 (s, 1H), 5.02 (s, 1H), 2.07 (s, 2H), 0.04 (s, 9H).14-008  (A) δ 8.63 (d, J = 5.1 Hz, 1H), 7.69 (t, J = 8.0 Hz, 1H),7.2-7.4 (m, 5H), 5.99 (s, 1H), 5.64 (s, 1H). 14-009  (A) δ 7.25-7.6 (m,3H), 6.04 (s, 1H), 5.80 (s, 1H). 14-010  (B) δ 7.24 (s, 1H), 7.20 (s,1H), 7.14 (s, 1H), 5.97 (s, 1H), 5.77 (s, 1H), 2.36 (s, 3H). 14-012  (A)δ 7.40 (d, J = 6.3 Hz, 2H), 6.04 (s, 1H), 5.79 (s, 1H). 14-013  (B) δ7.54 (s, 2H), 6.06 (s, 1H), 5.83 (s, 1H). 14-016  (A) δ 7.70 (s, 1H),7.52 (s, 2H), 6.04 (s, 1H), 5.80 (s, 1H). 14-018  (A) δ 7.65 (s, 1H),7.62 (s, 1H), 7.58 (s, 1H), 6.11 (s, 1H), 5.87 (s, 1H). 14-020  (A) δ7.69 (d, J = 6.3 Hz, 1H), 7.58 (d, J = 5.7 Hz, 1H), 6.10 (s, 1H), 5.83(s, 1H). 14-021  (A) δ 7.2-7.45 (m, 4H), 5.98 (s, 1H), 5.78 (s, 1H),2.93 (dd, J = 10.8, 7.8 Hz, 1H), 2.01 (dd, J = 10.8, 7.8 Hz, 1H), 1.87(t, J = 7.8 Hz, 1H). 14-022  (B) δ 7.35-7.45 (m, 2H), 7.2-7.3 (m, 2H),6.09 (d, J = 53.2 Hz, 1H), 6.03 (s, 1H), 5.82 (s, 1H). 14-023  (B) δ7.2-7.5 (m, 6H), 6.95-7.1 (m, 3H), 5.93 (s, 1H), 5.77 (s, 1H), 5.17 (s,2H). 14-024  (A) δ 7.57 (d, J = 2.7 Hz, 1H), 7.2-7.55 (m, 4H), 6.9-7.15(m, 3H), 5.96 (s, 1H), 5.78 (s, 1H), 5.19 (s, 2H). 14-025  (A) δ 8.27(s, 1H), 7.99 (s, 1H), 7.15-7.6 (m, 4H), 6.00 (s, 1H), 5.83 (s, 1H).14-026  (A) δ 7.74 (s, 1H), 7.69 (d, J = 7.7 Hz, 1H), 7.58 (d, J = 7.7Hz, 1H), 7.46 (t, J = 7.7 Hz, 1H), 6.04 (s, 1H), 5.82 (s, 1H). 14-027 (A) δ 8.34 (s, 1H), 8.25 (d, J = 8.0 Hz, 1H), 7.79 (d, J = 8.0 Hz, 1H),7.60 (t, J = 8.0 Hz, 1H), 6.14 (s, 1H), 5.93 (s, 1H).

Test Examples

Next, usefulness of the compound of the present invention as a pesticideis specifically explained in the following Test Examples to which thepresent invention is not limited.

Test Example 1 Insecticidal Test Against Cabbage Moth

A 10% emulsifiable concentrate (depending on the compounds, 10% wettablepowder was applied for the test) of the compound of the presentinvention was diluted with water containing a spreading agent to preparea chemical solution with a concentration of 500 ppm. To the chemicalsolution was dipped leaves of cabbage for about 10 seconds, and afterair-drying, they were placed in a laboratory dish, then 5-cabbage moth(Plutella xylostella) in the stage of second instar larva per the dishwere released therein, and the dish was covered with a lid and containedat a thermostat chamber at 25° C. A number of dead insect(s) after 6days was counted and a rate of dead insects was calculated by thefollowing calculation equation. Incidentally, the test was carried outwith two districts. Rate of dead insects (%)=(Number of deadinsects/Number of released insects)×100

As a result, the following compounds showed an insecticidal rate of 80%or more among the compounds tested.The compounds of the present invention:No.1-005,1-006,1-015,1-016,1-025,1-031,1-040,1-041,1-053,1-055˜1-058,1-062˜1-074,1-076,1-077,1-079˜1-096,1-098,1-101,1-102,1-104˜1-110,1-113,1-114,1-116˜1-140,1-145˜1-147,1-149˜1-157,1-159˜1-161,1-166˜1-168,1-171,1-172,1-174,1-175,1-176*,1-177*,1-178˜1-184,1-185*,1-187,1-188*,1-189*,1-190,1-194,1-196,1-199,1-206*,1-207,1-209,1-212,1-214,1-215,1-225,1-226,2-001˜2-005,2-011˜2-021,2-022*,2-024˜2-027,2-028**,2-029**,2-030,2-031,2-032*,2-033,2-034**,2-035**,2-036˜2-041,2-042**,2-043,2-044**,2-045**,2-046**,2-047*,2-048**,2-049**,2-050*,2-051*,2-052*,2-053,2-054**,2-055**,2-057*,2-058*,2-059*,2-060*,2-061*,2-062*,2-063*,2-064,2-065*,2-066,2-067*,2-068*,2-069,3-002˜3-004,3-006,3-007,3-012,3-018,3-023,3-025˜3-028,3-030˜3-035,3-037,3-038,3-040,3-043,3-044,3-046,3-047,3-050,3-055,3-058*,3-060,3-061*,3-062˜3-067,3-068*,3-069,3-070*,3-071*,3-073˜3-075,3-077˜3-081,3-084,3-085*,3-086*,3-087˜3-089,3-090*,3-091*,3-092*,3-093*,3-094˜3-098,3-100*,3-102˜3-104,3-105*,3-106˜3-108,3-109*,3-110*,3-111*,3-112*,3-113*,3-114,3-115,3-116*,3-117,3-119˜3-127,3-129,3-131,3-132*,3-133˜3-136,3-138˜3-141,3-143,3-146,3-148,3-150,3-151**,4-002,4-003*,4-004*,4-005,4-006*,4-008˜4-010,5-001*,5-002*,5-003*,5-004*,5-005*,5-006,5-007,5-008*,5-009*,5-010*,5-011*,5-012*,5-013*,5-014*,5-015*,5-016,5-017,5-019,5-022*,5-023*,5-029*,5-030˜5-035,5-036*,5-037*,5-038*,5-039*,5-040*,5-041*,5-042,5-043,5-044*,5-045*,5-046*,5-047*,5-048*,5-049*,5-050*,5-051*,5-052*,5-053*,5-054˜5-056,5-057*,5-058*,5-059*,5-060*,5-061*,5-062*,5-063*,5-064*,5-065*,5-066,5-067*,5-068*,5-069*,5-070*,5-071*,5-072*,5-073*,5-074*,5-075,5-075(+)*,5-075(−),5-076*,5-077*,5-078*,5-079˜5-082,5-083*,5-084,5-085*,5-086*,5-087*,5-088*,5-089*,5-090**,5-091*,5-092*,5-093*,5-094*,5-095,5-097,5-098,5-099*,5-100*,5-101*,5-102*,5-103*,5-104*,5-105*,5-106˜5-108,5-109*,5-110,5-111*,5-112*,5-113*,5-114*,5-115,5-116,5-117*,5-118*,5-119*,5-120**,5-121*,5-122*,5-123*,5-124**,5-125,5-126*,5-127,5-128*,5-129,5-130*,5-131˜5-133,5-134*,5-135˜5-137,5-138*,5-139*,5-140*,5-141*,5-142*,5-143,5-144*,5-145*,5-146,5-147*,5-148*,5-149,5-150,5-151*,5-151(+)*,5-151(−),5-152˜5-155,5-156*,5-158,5-159,5-160*,5-161**,5-162*,5-163,5-164,5-165*,5-166*,5-167,5-168**,5-169*,5-170˜5-172,5-173**,5-174**,5-175,5-176*,5-177,5-178,5-179*,5-180*,5-181*,5-182*,5-183*,5-184,5-185*,5-186*,5-187*,5-188*,5-189**,5-189(+)*,5-189(−),5-190(+)*,5-190(−),5-191*,5-192*,5-193*,5-194*,5-195**,5-196**,5-197**,5-198˜5-200,5-201*,5-202*,5-203**,5-204,5-205*,5-206*,5-207,5-208**,5-209,5-210*,5-211*,5-212*,5-213*,5-214*,5-215*,5-216*,5-217**,5-218*,5-219*,5-219(+)*,5-219(−)*,5-220*,5-221*,5-222*,5-223*,5-224*,5-225*,5-226*,5-227*,5-228*,5-229*,5-230*,5-231*,5-232*,5-233*,5-234*,5-235**,5-236*,5-237,5-238*,5-239*,5-240*,5-241*,5-242*,5-243**,5-244,5-245*,5-246*,5-247*,5-248,5-249*,5-250,5-251*,5-252,5-253,5-254*,5-255,5-256*,5-257*,5-258**,5-259*,5-260,5-261*,5-262**,5-263**,5-264*,5-265*,5-266,5-267*,5-268*,5-270,5-271,5-272*,5-273*,5-274*,5-275*,5-276*,5-277*,5-278*,5-279*,5-280,5-281,5-282*,5-283*,5-284*,5-285*,5-286*,5-287,5-288*,5-289*,5-290,5-291*,5-292,5-293,5-294*,5-295*,5-296,5-298,5-299*,5-300*,5-301*,5-302,5-303*,5-304,5-305**,5-306*,5-307*,5-308**,5-309*,5-310**,5-311,5-312*,5-313*,5-314*,5-315*,5-316,5-317*,5-318*,5-319*,5-320*,5-321,5-322,5-323*,5-324˜5-326,5-328,5-329*,5-330*,5-331*,5-332*,5-333*,5-334*,5-335*,5-336*,5-337,5-338*,5-339*,5-340,5-341,5-342*,5-343*,5-344*,5-345,5-346*,5-347,5-349*,5-350˜5-352,5-353*,5-354*,5-355*,5-356*,5-357*,5-358*,5-359**,5-360*,5-361*,5-362*,5-363,5-366,5-372,5-374*,5-375*,5-376**,5-377**,5-378*,5-379**,5-380**,5-381**,5-383*,5-384*,5-385**,5-386**,5-387*,5-389*,5-390*,5-391,5-392*,5-393*,5-395*,5-396**,5-397*,5-398*,5-399*,5-400*,5-401*,5-402*,5-403˜5-407,5-408*,5-409,5-410*,5-411*,5-412*,5-413*,5-414,5-415*,5-416,5-417*,5-418*,5-419*,5-420*,5-421*,5-422*,5-423*,5-424*,5-425*,5-426*,5-427*,5-428*,5-429*,5-430*,5-431,5-432*,5-433*,5-434*,5-436˜5-438,5-439*,5-440*,5-441*,5-442*,5-443*,5-444*,5-445*,5-446*,5-447˜5-450,5-452*,5-453*,5-454*,5-455*,5-456,5-457,5-458*,5-459*,5-460*,5-461*,5-462*,5-463**,5-464**,5-465**,5-466**,5-467*,5-468**,5-469**,5-470**,5-471*,5-472*,5-473*,5-474*,5-475**,5-476*,5-477**,5-478**,5-479,5-480*,5-481˜5-486,5-487**,5-488**,5-489*,5-490˜5-493,5-494**,5-495**,5-496**,5-497**,5-498**,5-499**,5-500*,5-501˜5-505,5-507,5-508,5-509**,5-510**,5-511**,5-512*,5-513*,5-514*,5-515*,5-516*,5-517*,5-518,5-519*,5-520*,5-521*,5-522*,5-523*,5-524,5-525,5-526*,5-527*,5-528*,5-529*,5-530*,5-531*,5-532,5-533*,5-534,5-535,5-536*,5-537*,5-538*,5-539*,5-540,5-540(+)*,5-541*,5-541(R),5-541(S)*,5-542,5-543*,5-544*,5-545,5-546*,5-547*,5-548*,5-549*,5-550,5-551*,5-552*,5-553*,5-554*,5-555*,5-556,5-557*,5-558*,5-559˜5-565,5-566*,5-567,5-568*,5-569*,5-570*,5-571,5-572*,5-573*,5-574*,5-575*,5-576*,5-577*,5-578*,5-579*,5-580*,5-581*,5-582*,5-583*,5-584*,5-585*,5-586*,5-587*,5-588*,5-589*,5-590*,5-591,5-592,5-593*,5-594*,5-595*,5-596*,5-597*,5-598*,5-599*,5-600*,5-601*,5-602,5-603,5-604*,5-605**,5-606**,5-607*,5-608**,5-609,5-610,5-611*,5-612**,5-613**,5-614*,5-615*,5-616*,5-617*,5-618,5-619*,5-620˜5-622,5-623*,5-624*,5-625*,5-626,5-627**,5-628**,5-629*,5-630*,5-631*,5-632*,5-633*,5-634*,5-635*,5-636,5-637*,5-638*,5-639*,5-640,5-641*,5-642**,5-643*,5-644**,5-645*,5-646*,5-648*,5-651,5-653*,5-654*,5-655**,5-656**,5-657**,5-658,5-659*,5-660**,5-661*,5-662**,5-663,5-664**,5-665*,5-666**,5-667*,5-668**,5-669*,5-670*,5-671**,5-672**,5-674**,5-676**,5-678,5-684**,5-685**,5-686**,6-001*,6-002,6-003*,6-004**,6-005,6-006**,6-007*,6-008*,6-009,6-010,6-011*,6-012,6-013*,6-015**,6-016*,6-017*,6-018*,6-019*,6-020*,6-021*,6-022**,6-023*,6-024**,6-025,6-026*,6-027*,6-028*,6-029*,6-030,6-031*,6-032*,6-033*,6-034*,6-035*,6-036*,6-037*,6-038*,6-039*,6-040*,6-041*,6-042*,6-043*,6-044*,6-045*,6-046*,6-047*,6-048*,6-049*,6-050*,6-051*,6-052,6-053,6-054*,6-055*,6-056*,6-057,6-058*,6-059*,6-060**,6-061,6-062**,6-063*,6-064**,6-065**,6-066*,6-067**,6-071**,6-074*,6-075*,6-076*,6-077*,6-078*,6-079*,6-080*,6-080(+)*,6-080(−)*,6-082*,6-083*,6-084*,6-085˜6-088,6-089*,6-090*,6-091*,6-092**,6-093**,6-094**,6-095**,6-096*,6-097,6-099,6-100**,6-101**,6-102**,6-103**,6-104*,6-105,6-106*,6-108,6-109,6-110*,6-111*,6-112*,6-113,6-114*,6-115*,6-116,6-117˜6-120,6-121*,6-122,6-123*,6-124*,6-125**,6-126*,6-127,6-129*,6-130**,6-131**,6-132**,6-133**,7-001,7-002*,7-003*,7-004*,7-005*,7-006*,7-007*,7-008*,7-009*,7-010*,8-002*,8-003*,8-004,8-005,8-006*,8-007*,9-003,9-008˜9-011,10-001,10-002*,10-003˜10-005,10-006*,11-006,11-018,11-024,11-025*,11-026*,11-038,11-043,11-045,11-046,11-049*,11-050˜11-052,11-054,11-056,11-058˜11-062,11-066,11-075,11-088,11-089,11-098*,11-099*,11-101˜11-107,11-108*,11-109*,11-110˜11-117,11-119,11-120*,11-122,11-124*,11-125*,11-128,11-129,11-132,12-001,12-002,12-008.In the interim, the indication of “*” shows that the insecticidal testwas carried out by use of a chemical solution of a concentration of 100ppm, and the indication “*” shows that the insecticidal test was carriedout by use of a chemical solution of a concentration of 10 ppm.

Test Example 2 Insecticidal Test Against Common Cutworm

A 10% emulsifiable concentrate (depending on the compounds, 10% wettablepowder was applied for the test) of the compound of the presentinvention was diluted with water containing a spreading agent to preparea chemical solution with a concentration of 500 ppm. To the chemicalsolution was dipped leaves of cabbage for about 10 seconds, and afterair-drying, they were placed in a laboratory dish, then 5-common cutworm(Spodoptera litura) in the stage of second instar larva per the dishwere released therein, and the dish was covered with a lid and containedat a thermostat chamber at 25° C. A number of dead insect(s) after 6days was counted and a rate of dead insects was calculated by thecalculation equation similar to that in Test Example 1. Incidentally,the test was carried out with two districts.

As a result, the following compounds showed an insecticidal rate of 80%or more among the compounds tested.The compounds of the present invention:No.1-005,1-015,1-016,1-057,1-058,1-062,1-066,1-069,1-080,1-081,1-088,1-101,1-102,1-105˜1-109,1-118,1-122,1-123,1-125,1-127,1-129,1-130,1-132,1-153,1-156,1-157,1-166˜1-168,1-175,1-176,1-177*,1-182˜1-184,1-185*,1-188*,1-189*,1-194,1-206*,1-207,1-212,1-214,1-215,1-225,2-002,2-003,2-013,2-019˜2-021,2-022*,2-024˜2-026,2-028,2-029,2-031,2-032,2-034˜2-039,2-041,2-042,2-044˜2-046,2-047*,2-048,2-049,2-050*,2-051*,2-052*,2-054˜2-056,2-057*,2-058*,2-059*,2-061*,2-062*,2-064,2-065*,2-067*,2-068*,3-006,3-018,3-026,3-030,3-032˜3-035,3-037,3-043,3-044,3-047,3-058,3-060˜3-064,3-068*,3-069,3-070*,3-071*,3-072,3-078,3-079,3-081,3-083˜3-086,3-089,3-090*,3-091*,3-093*,3-094,3-095,3-098,3-100*,3-102,3-103,3-105*,3-106,3-107,3-109,3-110*,3-111*,3-112*,3-113*,3-114,3-115,3-116*,3-117,3-121,3-123˜3-126,3-129,3-131,3-132*,3-135,3-136,3-139,3-140,3-145,3-148,3-150,3-151**,4-003*,4-004,4-006*,4-010,5-001*,5-002*,5-003*,5-004*,5-005*,5-006,5-007,5-008*,5-009*,5-010,5-011,5-012*,5-013*,5-014*,5-015*,5-016,5-017,5-019,5-022*,5-023*,5-029*,5-032,5-034,5-035,5-036*,5-037*,5-038*,5-039*,5-040*,5-041*,5-042,5-045*,5-046*,5-047*,5-048*,5-049*,5-050*,5-051*,5-052*,5-053*,5-054,5-057*,5-058*,5-059*,5-060˜5-064,5-065*,5-066˜5-068,5-069*,5-070*,5-071*,5-072*,5-073˜5-075,5-075(+)*,5-076*,5-077*,5-078˜5-081,5-083*,5-084,5-085,5-086*,5-087*,5-088*,5-089*,5-090,5-091*,5-092*,5-093*,5-094*,5-099˜5-101,5-102*,5-103*,5-104*,5-105*,5-106,5-109,5-111*,5-112,5-113*,5-114*,5-115,5-116,5-117*,5-118,5-119*,5-120,5-121*,5-122˜5-126,5-128*,5-130,5-132˜5-134,5-136,5-137,5-138*,5-139*,5-140˜5-147,5-148*,5-149,5-151,5-151(+)*,5-152˜5-156,5-159˜5-169,5-171˜5-178,5-179*,5-180,5-181,5-182*,5-183*,5-184,5-185*,5-186*,5-187*,5-188*,5-189,5-189(+),5-191*,5-192*,5-193˜5-201,5-202*,5-203,5-204,5-205*,5-206*,5-207˜5-209,5-210*,5-211*,5-212*,5-213*,5-214*,5-215*,5-216*,5-217,5-218*,5-219*,5-219(+)*,5-219(−),5-220*,5-221,5-222*,5-223*,5-224*,5-225,5-226*,5-227*,5-228,5-229,5-230*,5-231,5-232*,5-233*,5-234*,5-235,5-236*,5-237*,5-239,5-240*,5-241*,5-242*,5-243˜5-245,5-246*,5-247*,5-249*,5-250,5-251,5-254*,5-256*,5-257˜5-259,5-261*,5-262,5-263,5-264*,5-265*,5-267,5-268*,5-269,5-271,5-272*,5-273*,5-274*,5-275˜5-277,5-278*,5-279*,5-280,5-282*,5-283*,5-284,5-285*,5-286*,5-288*,5-289*,5-291*,5-292,5-294*,5-295*,5-296,5-298,5-299*,5-300,5-301*,5-302,5-303,5-305,5-306*,5-307*,5-308˜5-311,5-312*,5-313*,5-314*,5-315*,5-316,5-317*,5-318*,5-319*,5-320˜5-322,5-323*,5-329*,5-330*,5-331*,5-332,5-333*,5-334*,5-335˜5-337,5-338*,5-339*,5-341,5-342,5-343*,5-344*,5-345,5-346,5-349*,5-351,5-353,5-354,5-355*,5-356˜5-359,5-360*,5-361*,5-362*,5-363,5-374*,5-375*,5-376,5-377,5-378*,5-379˜5-386,5-387*,5-389*,5-390*,5-392*,5-393*,5-395,5-396,5-397*,5-398*,5-399*,5-400*,5-401*,5-402*,5-405˜5-407,5-408*,5-409,5-410*,5-411*,5-412*,5-413*,5-415*,5-417*,5-418*,5-419*,5-420*,5-421*,5-422*,5-423*,5-424*,5-425*,5-426*,5-427*,5-428*,5-429*,5-430*,5-432*,5-433*,5-434*,5-437,5-438,5-439*,5-440*,5-441*,5-442*,5-443*,5-444*,5-446*,5-447,5-452*,5-453*,5-454*,5-455*,5-458*,5-459*,5-460*,5-461*,5-462*,5-463**,5-464**,5-465**,5-466**,5-467*,5-468**,5-469**,5-470**,5-471*,5-472*,5-473*,5-474*,5-475**,5-476*,5-477**,5-478**,5-479,5-480*,5-481˜5-486,5-487**,5-488**,5-489*,5-490˜5-493,5-494**,5-495**,5-496**,5-497**,5-498**,5-499**,5-500*,5-501,5-503,5-505,5-507,5-508,5-509**,5-511**,5-513*,5-514*,5-515*,5-516*,5-517*,5-518,5-519*,5-520*,5-521*,5-522*,5-523*,5-526*,5-527*,5-528*,5-529*,5-530*,5-531*,5-532,5-533*,5-535,5-536*,5-537*,5-538*,5-539*,5-540(+),5-541*,5-541(R),5-541(S)*,5-542,5-543*,5-545,5-546,5-548*,5-549*,5-551*,5-552*,5-553*,5-554*,5-555*,5-556,5-557*,5-558*,5-559,5-560,5-562,5-565,5-566*,5-568*,5-569*,5-570*,5-571,5-572*,5-573*,5-574*,5-575*,5-576*,5-577*,5-578*,5-579*,5-580*,5-581*,5-582*,5-583*,5-584*,5-585*,5-586*,5-587*,5-588*,5-589*,5-590*,5-592,5-593*,5-594*,5-595*,5-596*,5-598*,5-599*,5-600*,5-601*,5-602,5-603,5-604*,5-605**,5-606**,5-607*,5-608**,5-609,5-610,5-611*,5-612**,5-613**,5-614*,5-615*,5-616*,5-617*,5-618,5-619*,5-621,5-623*,5-624*,5-625*,5-626,5-627**,5-628**,5-629*,5-630*,5-631*,5-632*,5-633*,5-634*,5-635*,5-636,5-637*,5-638*,5-639*,5-641*,5-642**,5-643*,5-644**,5-645*,5-646*,5-647*,5-648*,5-650,5-651,5-653*,5-654*,5-655**,5-656**,5-657**,5-659*,5-660**,5-661*,5-662**,5-664**,5-665*,5-666**,5-667*,5-668**,5-669*,5-670*,5-671**,5-672**,5-674**,5-676**,5-678,5-684**,5-685**,5-686**,6-001*,6-002,6-003*,6-004˜6-006,6-007*,6-008*,6-010,6-012,6-013,6-015,6-016,6-017*,6-018,6-019*,6-020*,6-021*,6-022˜6-025,6-026*,6-027*,6-028˜6-030,6-031*,6-032*,6-033*,6-034*,6-035*,6-036˜6-038,6-039*,6-040,6-041,6-042*,6-043*,6-044,6-045,6-046*,6-047*,6-048*,6-049*,6-050*,6-051*,6-053,6-054*,6-055*,6-056,6-058˜6-067,6-071,6-074*,6-075*,6-076*,6-077*,6-078*,6-079*,6-080*,6-080(+)*,6-080(−)*,6-082*,6-083*,6-084*,6-086,6-087,6-089*,6-090*,6-091*,6-092**,6-093**,6-094**,6-095**,6-096*,6-098*,6-099,6-100**,6-101**,6-102**,6-103**,6-104*,6-105,6-106*,6-110*,6-111*,6-112*,6-114*,6-120,6-121*,6-123*,6-124*,6-125**,6-126*,6-129*,6-130**,6-131**,6-132**,6-133**,7-001,7-002*,7-003*,7-004*,7-005*,7-006*,7-007*,7-008*,7-009*,7-010*,8-002*,8-003*,8-004,8-005,8-006*,8-007*,9-009,10-001˜10-005,10-006*,11-024,11-025*,11-026*,11-038,11-049*,11-052,11-055,11-056,11-061,11-062,11-066,11-070,11-098*,11-099*,11-108*,11-109*,11-119,11-120*,11-124*,11-125*,11-129,12-001,12-002,12-008.In the interim, the indication of “*” shows that the insecticidal testwas carried out by use of a chemical solution of a concentration of 100ppm.

Test Example 3 Insecticidal Test Against Beet Armyworm

A 10% emulsifiable concentrate (depending on the compounds, 10% wettablepowder was applied for the test) of the compound of the presentinvention was diluted with water containing a spreading agent to preparea chemical solution with a concentration of 100 ppm. To the chemicalsolution was dipped leaves of cabbage for about 10 seconds, and afterair-drying, they were placed in a laboratory dish, then 5-beet armyworm(Spodoptera exigua) in the stage of second instar larva per the dishwere released therein, and the dish was covered with a lid and containedat a thermostat chamber at 25° C. A number of dead insect(s) after 6days was counted and a rate of dead insects was calculated by thecalculation equation similar to that in Test Example 1. Incidentally,the test was carried out with two districts.

As a result, the following compounds showed an insecticidal rate of 80%or more among the compounds tested.The compounds of the present invention: No.1-015,1-016,1-057,1-058,1-062˜1-064,1-066,1-080,1-081,1-088,1-102,1-105,1-106,1-109,1-118,1-122,1-123,1-125,1-127,1-151,1-153,1-155˜1-157,1-166,1-175,1-189,1-207,1-214,1-215,2-003,2-019,2-020,3-026,3-027,3-030,3-032,3-037,3-060,3-091,3-093,3-095,3-109,3-110,3-112,3-125,5-001˜5-005,5-008,5-009,5-029,5-036,5-037,5-040,5-041,5-045,5-046,5-048,5-049,5-050,5-052,5-053,5-057˜5-059,5-061˜5-065,5-067˜5-069,5-071,5-073˜5-075,5-075(+),5-076,5-083,5-086˜5-089,5-091,5-092,5-094,5-111,5-113,5-117˜5-119,5-122,5-138˜5-142,5-147,5-148,5-151,5-160,5-165,5-174,5-182,5-183,5-185˜5-188,5-189(+),5-202,5-205,5-210˜5-212,5-214˜5-216,5-218,5-219,5-219(+),5-220,5-223,5-226,5-227,5-230,5-232˜5-234,5-236,5-239,5-241,5-247,5-251,5-257,5-261,5-264,5-268,5-273˜5-275,5-279,5-282,5-283,5-285,5-286,5-288,5-291,5-294,5-295,5-301,5-306,5-307,5-309,5-310,5-312˜5-315,5-320,5-321,5-323,5-331˜5-334,5-339,5-341,5-355˜5-357,5-360˜5-362,5-374,5-375,5-378,5-387,5-389,5-390,5-397,5-398,5-412,5-429,5-433,5-440,5-474,5-476,5-478,5-480,5-488,5-494,5-495,5-588,5-604,5-638,5-642,6-017˜6-021,6-026,6-027,6-031,6-033˜6-041,6-043˜6-045,6-048,6-049,6-058,6-059,6-063˜6-066,6-074˜6-076,6-095,6-131,7-002,7-003,7-005˜7-009,8-002,11-024,11-025,11-026.

Test Example 4 Insecticidal Test Against Oriental Tea Tortix

A 10% emulsifiable concentrate (depending on the compounds, 10% wettablepowder was applied for the test) of the compound of the presentinvention was diluted with water containing a spreading agent to preparea chemical solution with a concentration of 100 ppm. To the chemicalsolution was dipped leaves of cabbage for about 10 seconds, and afterair-drying, they were placed in a laboratory dish, then 5-oriental teatortix (Homona magnanima) in the stage of second instar larva per thedish were released therein, and the dish was covered with a lid andcontained at a thermostat chamber at 25° C. A number of dead insect(s)after 6 days was counted and a rate of dead insects was calculated bythe calculation equation similar to that in Test Example 1.Incidentally, the test was carried out with two districts.

As a result, the following compounds showed an insecticidal rate of 80%or more among the compounds tested.The compounds of the present invention: No.1-015,1-016,1-057,1-058,1-062,1-080,1-105,1-107,1-0122,1-123,1-125,1-127,1-153,1-156,1-189,1-207,1-214,1-215,2-003,2-034,2-035,2-051,2-052,3-037,3-060,3-095,3-110,3-112,3-125,3-129,4-003,5-001,5-003˜5-005,5-008,5-009,5-012,5-013,5-022,5-029,5-037,5-040,5-041,5-045˜5-050,5-052,5-053,5-057˜5-059,5-061˜5-065,5-069˜5-071,5-073,5-075,5-075(+),5-076,5-077,5-083,5-086˜5-090,5-092˜5-094,5-102,5-103,5-111,5-113,5-114,5-117,5-119,5-121,5-122,5-138˜5-142,5-147,5-148,5-151,5-151(+),5-156,5-160,5-161,5-165,5-166,5-180,5-182,5-183,5-185,5-187,5-188,5-189(+),5-202,5-205,5-208,5-210˜5-212,5-214˜5-216,5-218,5-219,5-219(+),5-220,5-221,5-223,5-226˜5-228,5-230,5-232˜5-234,5-236,5-240˜5-242,5-246,5-247,5-251,5-254,5-273˜5-275,5-279,5-282,5-283,5-285,5-286,5-288,5-289,5-291,5-294,5-295,5-301,5-306,5-307,5-310,5-312,5-313,5-315,5-319,5-321,5-323,5-329,5-330,5-338,5-339,5-341,5-356,5-357,5-359,5-360,5-362,5-374,5-375,5-378,5-379,5-381,5-387˜5-390,5-392,5-393,5-395˜5-399,5-401,5-412,5-418,5-419,5-426,5-429,5-430,5-433,5-434,5-441,5-458˜5-461,5-463˜5-465,5-468,5-470,5-472,5-474,5-476˜5-478,5-480,5-488,5-494,5-515,5-519,5-523,5-539,5-541,5-541(S),5-553,5-554,5-576,5-579,5-585,5-588,5-594,5-601,5-604,5-606,5-612,5-617,5-638,5-642,5-655,5-656,6-001,6-003,6-017,6-018,6-020,6-021,6-027,6-031,6-033˜6-035,6-038˜6-041,6-043,6-066,6-075,6-076,6-081,6-093,6-095,6-124,6-131,7-002˜7-009,8-002,11-024,11-026.

Test Example 5 Insecticidal Test Against Corn Earworm

A 10% emulsifiable concentrate (depending on the compounds, 10% wettablepowder was applied for the test) of the compound of the presentinvention was diluted with water containing a spreading agent to preparea chemical solution with a concentration of 100 ppm. To the chemicalsolution was dipped leaves of cabbage for about 10 seconds, and afterair-drying, they were placed in a laboratory dish, then 1-corn earworm(Helicoverpa armigera) in the stage of second instar larva per the dishwere released therein, and the dish was covered with a lid and containedat a thermostat chamber at 25° C. A number of dead insect(s) after 6days was counted and a rate of dead insects was calculated by thecalculation equation similar to that in Test Example 1. Incidentally,the test was carried out with twelve districts.

As a result, the following compounds showed an insecticidal rate of 80%or more among the compounds tested.The compounds of the present invention: No.1-066,1-153,1-156,1-207,1-214,1-215,2-034,2-035,2-042,2-055,2-057,2-059,2-062,2-063,2-067,2-068,3-027,3-030,3-032,3-086,3-095,3-109,3-110,3-112,3-151,5-008,5-009,5-022,5-040,5-046,5-047,5-049,5-050,5-052,5-053,5-057˜5-059,5-061˜5-063,5-065,5-068,5-070,5-071,5-075,5-075(+),5-076,5-077,5-083,5-086˜5-089,5-099˜5-101,5-109,5-113,5-117,5-120˜5-122,5-126,5-138,5-139,5-141,5-142,5-147,5-148,5-151,5-151(+),5-156,5-160,5-165,5-169,5-177,5-180,5-185,5-189(+),5-193,5-208,5-210˜5-212,5-214˜5-219,5-219(+),5-223,5-227,5-228,5-230,5-231,5-233,5-234,5-236,5-241,5-245,5-246,5-249,5-251,5-254,5-261,5-264,5-269,5-273˜5-275,5-279,5-284,5-286,5-291,5-294,5-295,5-306,5-307,5-309,5-310,5-312˜5-315,5-319,5-323,5-331˜5-336,5-338,5-339,5-341,5-353˜5-355,5-357,5-359,5-360,5-374,5-375,5-378˜5-381,5-383,5-384,5-387,5-389,5-390,5-393,5-395,5-397˜5-400,5-408˜5-413,5-415,5-420˜5-424,5-426,5-427,5-429,5-433,5-434,5-440,5-443,5-446,5-452˜5-454,5-458˜5-470,5-473˜5-481,5-483,5-484,5-487˜5-489,5-494˜5-499,5-508˜5-511,5-513,5-515˜5-517,5-519,5-522,5-523,5-526˜5-529,5-531˜5-533,5-538,5-539,5-541,5-541(S),5-543,5-548,5-549,5-558˜5-560,5-566,5-568,5-570,5-572˜5-577,5-579˜5-589,5-595,5-599˜5-601,5-604,5-606˜5-608,5-611,5-612,5-614˜5-619,5-623˜5-625,5-627˜5-639,5-641˜5-646,5-654˜5-657,5-660˜5-662,5-664˜5-668,5-671,5-672,5-674,5-676,5-684,5-685,6-003,6-004,6-016˜6-019,6-021,6-023,6-024,6-026,6-027,6-031,6-033˜6-041,6-043˜6-045,6-048,6-049,6-056,6-066,6-074˜6-080,6-080(+),6-080(−),6-081˜6-084,6-091˜6-095,6-098,6-100,6-102˜6-106,6-110,6-111,6-124,6-126,6-130˜6-132,7-002˜7-009,8-002,8-005˜8-007,10-006,11-024,11-125,11-130.

Test Example 6 Insecticidal Test Against Peach Fruit Moth

A 10% emulsifiable concentrate (depending on the compounds, 10% wettablepowder was applied for the test) of the compound of the presentinvention was diluted with water containing a spreading agent to preparea chemical solution with a concentration of 100 ppm. To the chemicalsolution was dipped apple young fruits on which peach fruit moth(Carpocina sasakii) laid eggs (20-egg/fruit) for about 10 seconds, andafter air-drying, they were placed in a laboratory dish, and the dishwas covered with a lid and contained at a thermostat chamber at 25° C. Anumber of dead insect(s) after 20 days was counted and a rate of deadinsects was calculated by the calculation equation similar to that inTest Example 1. Incidentally, the test was carried out with twodistricts.

As a result, the following compounds showed an insecticidal rate of 80%or more among the compounds tested.The compounds of the present invention: No.5-049,5-050,5-070,5-076,5-083,5-088,5-111,5-148,5-219,5-219(+),5-221,5-234,5-286,5-291,5-323,5-360,5-387,5-390,5-398,5-480,5-494,6-027,6-039,7-008.

Test Example 7 Insecticidal Test Against Frankliniella occidentalis

A wet filter paper was laid in a styrol cup having an inner diameter of7 cm, a leaf of a common bean cut out so as to have the same diameterwas laid thereon, and 10-Frankliniella occidentalis with first instarlarva per leaf was inoculated thereon. A 10% emulsifiable concentrate(depending on the compounds, 10% wettable powder was applied for thetest) of the compound of the present invention was diluted with watercontaining a spreading agent to prepare a chemical solution with aconcentration of 500 ppm. The chemical solution was sprayed with arotating spray tower in an amount of 2.5 ml per styrol cup, and thestyrol cups were covered with lids and contained at a thermostat chamberat 25° C. A number of dead insect(s) after 2 days was counted and a rateof dead insects was calculated by the calculation equation similar tothat in Test Example 1. Incidentally, the test was carried out with twodistricts.

As a result, the following compounds showed an insecticidal rate of 80%or more among the compounds tested.The compounds of the present invention: No.1-175,1-177˜1-179,1-182,2-020,2-022,2-028*,2-029*,2-032,2-033,2-034*,2-035*,2-037*,2-038*,2-039*,2-040*,2-041*,2-042*,2-043*,2-044*,2-045*,2-046*,2-047,2-048*,2-049*,2-050˜2-052,2-057˜2-068,3-068,3-072*,3-080,3-084˜3-086,3-090,3-093,3-105,3-107,3-109,3-110,3-1,2,3-114,3-122˜3-125,3-132,3-135,3-136,3-151,4-004,4-006,5-001,5-003,5-009,5-013,5-022,5-023,5-029,5-037˜5-041,5-044˜5-053,5-057˜5-075,5-075(+),5-076˜5-078,5-081˜5-089,5-090*,5-091˜5-094,5-099˜5-105,5-109,5-111˜5-119,5-120*,5-121˜5-123,5-124*,5-126˜5-128,5-129*,5-130,5-131*,5-134,5-137˜5-142,5-143*,5-144,5-145,5-146*,5-147,5-148,5-150,5-151,5-151(+),5-153*,5-154,5-156,5-158˜5-160,5-161*,5-162,5-164˜5-166,5-167*,5-168*,5-169,5-171,5-172*,5-178˜5-188,5-189(+),5-190(+),5-191˜5-194,5-201,5-202,5-205˜5-207,5-208*,5-210˜5-216,5-217*,5-218,5-219,5-219(+),5-219(−),5-220˜5-234,5-236˜5-242,5-244˜5-247,5-249,5-251˜5-254,5-255*,5-256,5-257,5-258*,5-259˜5-261,5-264,5-265,5-269*,5-270,5-271*,5-272˜5-283,5-284˜5-289,5-291,5-292,5-294,5-295,5-297,5-299,5-300,5-301,5-302*,5-303,5-306,5-307,5-309,5-310*,5-311˜5-315,5-318,5-319,5-321˜5-323,5-329˜5-336,5-338,5-339,5-341˜5-346,5-348,5-349,5-353˜5-358,5-360˜5-362,5-374,5-375,5-378,5-379*,5-380*,5-381*,5-383,5-384,5-385*,5-387˜5-393,5-395,5-396*,5-397˜5-401,5-403˜5-406,5-408˜5-413,5-415,5-417˜5-430,5-432˜5-434,5-439˜5-443,5-445,5-446,5-449,5-452,5-453,5-455,5-458˜5-503,5-507˜5-512,5-514˜5-516,5-518,5-519,5-521˜5-525,5-527˜5-534,5-537˜5-539,5-541,5-541(S),5-542,5-543,5-545˜5-549,5-550˜5-562,5-564,5-565,5-567˜5-576,5-579˜5-590,5-592,5-599˜5-601,5-604˜5-609,5-611,5-612,5-614˜5-619,5-621,5-623,5-624,5-626˜5-639,5-641˜5-648,5-650,5-651,5-653˜5-672,5-674,5-676,5-678,5-684˜5-686,6-001˜6-003,6-004*,6-005*,6-006*,6-007˜6-013,6-015*,6-016˜6-021,6-022*,6-023,6-024*,6-025*,6-026˜6-050,6-054˜6-056,6-058,6-059,6-063,6-066,6-070,6-071*,6-074˜6-080,6-080(+),6-080(−),6-081˜6-086,6-089˜6-111,6-113˜6-115,6-117,6-119˜6-124,6-126,6-127,6-129˜6-133,7-001,7-003˜7-010,8-002,8-003,8-005,8-006,10-002,10-005,10-006,11-024˜11-026,11-043,11-045,11-054˜11-056,11-059,11-070,11-089,11-099,11-107,11-114,11-120,11-125,11-128˜11-130,11-132,12-002,12-007,12-008.In the interim, the indication of “*” shows that the insecticidal testwas carried out by use of a chemical solution of a concentration of 100ppm.

Test Example 8 Insecticidal Test Against Thrips palmi

A wet filter paper was laid in a styrol cup having an inner diameter of7 cm, a leaf of a common bean cut out so as to have the same diameterwas laid thereon, and 10-Thrips palmi in the stage of adult per leaf wasinoculated thereon. A 10% emulsifiable concentrate (depending on thecompounds, 10% wettable powder was applied for the test) of the compoundof the present invention was diluted with water containing a spreadingagent to prepare a chemical solution with a concentration of 100 ppm.The chemical solution was sprayed with a rotating spray tower in anamount of 2.5 ml per styrol cup, and the styrol cups were covered withlids and contained at a thermostat chamber at 25° C. A number of deadinsect(s) after 2 days was counted and a rate of dead insects wascalculated by the calculation equation similar to that in TestExample 1. Incidentally, the test was carried out with two districts.

As a result, the following compounds showed an insecticidal rate of 80%or more among the compounds tested.The compounds of the present invention: No.1-179,1-196,2-022,2-024˜2-026,2-028,2-029,2-033,2-035,2-039,2-044˜2-048,2-050˜2-052,2-057˜2-059,2-061,2-063,2-065,2-067,3-079,3-085,3-086,3-091,3-110,3-112,3-124,3-131,3-148,3-151,4-003˜4-005,4-010,5-001,5-003,5-006,5-008,5-012˜5-015,5-022,5-023,5-029,5-036,5-037,5-040,5-045˜5-053,5-057˜5-063,5-065,5-067,5-068,5-070˜5-075,5-075(+),5-076˜5-079,5-081˜5-084,5-086˜5-093,5-099,5-102˜5-104,5-111˜5-114,5-117˜5-121,5-124,5-128˜5-130,5-137˜5-148,5-151,5-151(+),5-153,5-156,5-160˜5-162,5-165,5-166,5-179,5-180,5-182˜5-186,5-188,5-189(+),5-193,5-202,5-205,5-206,5-208˜5-210,5-214˜5-216,5-218,5-219,5-219(+),5-220,5-224˜5-226,5-228˜5-230,5-232˜5-234,5-236,5-238,5-239,5-242,5-246,5-247,5-251,5-256˜5-258,5-261,5-264,5-269,5-273˜5-276,5-278,5-279,5-280,5-282,5-283,5-285,5-286,5-288,5-289,5-291,5-294,5-295,5-299,5-303,5-306,5-309,5-310,5-312˜5-314,5-319,5-322,5-323,5-329,5-330,5-332,5-334,5-335,5-338,5-339,5-346,5-349,5-353˜5-362,5-374,5-375,5-378˜5-381,5-383˜5-385,5-387,5-389,5-390,5-395˜5-401,5-408˜5-413,5-415,5-418˜5-424,5-426,5-427,5-429,5-430,5-432˜5-434,5-439˜5-443,5-446,5-452˜5-455,5-458˜5-470,5-471˜5-492,5-494˜5-501,5-508˜5-513,5-515,5-516,5-519,5-521˜5-523,5-525,5-527˜5-531,5-533,5-536,5-538,5-539,5-541,5-541(S),5-543,5-547,5-549,5-553˜5-555,5-560,5-564,5-568˜5-570,5-572˜5-576,5-579,5-581,5-582,5-584˜5-590,5-593,5-598˜5-601,5-604˜5-609,5-611˜5-613,5-616˜5-619,5-621,5-623˜5-625,5-627˜5-639,5-641˜5-648,5-650,5-651,5-655˜5-657,5-659˜5-662,5-664˜5-669,5-672,5-674,5-676,5-684,5-685,6-001,6-003˜6-008,6-015,6-017˜6-024,6-026˜6-035,6-037˜6-041,6-043˜6-045,6-047˜6-049,6-054˜6-056,6-058,6-059,6-063,6-066,6-070,6-073˜6-080,6-080(46-080(−),6-081˜6-084,6-089,6-090,6-092˜6-096,6-098˜6-107,6-109˜6-111,6-114,6-115,6-120,6-121,6-123,6-124,6-130˜6-133,7-003,7-005˜7-009,8-002,8-006,8-007,9-011,10-002,10-006,11-025,11-026,11-054,11-056,11-059,11-125,11-129,12-002,12-008.

Test Example 9 Insecticidal Test Against Eysarcoris lewisi

A 10% emulsifiable concentrate (depending on the compounds, 10% wettablepowder was applied for the test) of the compound of the presentinvention was diluted with water containing a spreading agent to preparea chemical solution with a concentration of 500 ppm. To the chemicalsolution was dipped leave sheaths of rice for about 10 seconds, andafter air-drying, they were placed in a test tube, then 5-Eysarcorislewisi in the stage of first instar larva per the test tube werereleased therein, and the test tube was covered with a sponge andcontained at a thermostat chamber at 25° C. A number of dead insect(s)after 2 days was counted and a rate of dead insects was calculated bythe calculation equation similar to that in Test Example 1.Incidentally, the test was carried out with two districts.

As a result, the following compounds showed an insecticidal rate of 80%or more among the compounds tested.The compounds of the present invention:No.1-015,1-050,1-051,1-175,1-209,2-029,2-034,2-035,2-042,2-044˜2-052,2-054,2-055,2-057˜2-059,2-061,2-062,2-065,2-067,2-068,3-047,3-068,3-070˜3-072,3-086,3-090,3-093,3-106,3-109˜3-1,2,3-114,3-125,3-131,3-151,5-001,5-003,5-005,5-008,5-009,5-013˜5-015,5-017,5-022,5-023,5-026,5-029,5-037˜5-041,5-045˜5-053,5-058˜5-065,5-067˜5-069,5-071˜5-075,5-075(+),5-076˜5-078,5-081,5-083,5-084˜5-094,5-099˜5-105,5-111˜5-114,5-116˜5-122,5-124,5-126,5-128,5-130,5-134,5-137˜5-142,5-144,5-145,5-147,5-148,5-150,5-151,5-151(+),5-154,5-156,5-158˜5-162,5-165,5-166,5-168,5-169,5-171,5-173,5-174,5-179˜5-189,5-189(+),5-191,5-195˜5-197,5-203,5-205,5-206,5-208˜5-210,5-212˜5-216,5-218,5-219,5-219(+),5-220˜5-230,5-232,5-233,5-235,5-236,5-238˜5-247,5-249,5-251,5-254,5-256˜5-262,5-264,5-265,5-273˜5-279,5-283,5-285,5-286,5-288,5-289,5-291,5-294,5-295,5-299˜5-301,5-304˜5-310,5-312˜5-315,5-318˜5-321,5-323,5-329,5-330,5-332,5-334,5-335,5-338,5-339,5-341˜5-344,5-346,5-348,5-353˜5-360,5-362,5-374˜5-387,5-389,5-390,5-392,5-393,5-395˜5-401,5-403˜5-405,5-408˜5-413,5-415,5-417˜5-424,5-426˜5-429,5-431˜5-434,5-440,5-443,5-445,5-446,5-448,5-452˜5-455,5-457˜5-465,5-467˜5-470,5-472˜5-478,5-480,5-487˜5-489,5-491,5-492,5-494˜5-500,5-505,5-509,5-510,5-512,5-515˜5-517,5-519˜5-523,5-526˜5-533,5-537˜5-539,5-541,5-541(S),5-543,5-546,5-547,5-549,5-551˜5-558,5-562,5-568˜5-570,5-572˜5-577,5-579,5-582˜5-588,5-593,5-595,5-598,5-600,5-601,5-604,5-606,5-611,5-612,5-614˜5-617,5-619,5-621,5-623,5-627,5-631,5-635˜5-638,5-642,5-643,5-646,5-648,5-654˜5-657,5-660,5-661,5-664,5-668,5-670,5-672,5-674,5-684˜5-686,6-001,6-006˜6-013,6-015˜6-024,6-026˜6-029,6-031˜6-051,6-054˜6-056,6-058˜6-060,6-062˜6-067,6-070,6-071,6-074˜6-080,6-080(46-080(−),6-081˜6-086,6-089˜6-093,6-095,6-098˜6-103,6-110˜6-112,6-114˜6-118,6-121,6-124,6-129˜6-132,7-002˜7-010,10-006,11-060,11-098,11-125.

Test Example 10 Insecticidal Test Against Brown Rice Planthopper

A 10% emulsifiable concentrate (depending on the compounds, 10% wettablepowder was applied for the test) of the compound of the presentinvention was diluted with water containing a spreading agent to preparea chemical solution with a concentration of 500 ppm. To the chemicalsolution was dipped leave sheaths of rice for about 10 seconds, andafter air-drying, they were placed in a test tube, then 5-brown riceplanthopper (Nilaparvata lugens) in the second instar larva per the testtube were released therein, and the test tube was covered with a spongeand contained at a thermostat chamber at 25° C. A number of deadinsect(s) after 6 days was counted and a rate of dead insects wascalculated by the calculation equation similar to that in TestExample 1. Incidentally, the test was carried out with two districts.

As a result, the following compounds showed an insecticidal rate of 80%or more among the compounds tested.The compounds of the present invention: No.1-005˜1-007,1-017,1-061,1-154,1-175,1-185,1-188,1-189,2-018,2-020,2-025˜2-027,2-029,2-033,2-034,2-036,2-044,2-046,2-051,2-052,2-054,2-057˜2-059,2-062,2-065,2-068,3-013,3-068,3-070,3-072,3-075,3-109,3-112,3-125,3-151,5-001,5-003,5-009,5-013,5-015,5-023,5-029,5-040,5-041,5-049,5-050,5-053,5-058,5-060,5-061,5-063,5-065˜5-068,5-070˜5-074,5-075(+),5-076,5-077,5-080,5-081,5-083,5-084,5-086˜5-088,5-090˜5-094,5-099,5-102,5-106,5-111,5-113,5-117˜5-120,5-130,5-138˜5-148,5-151,5-151(+),5-152˜5-156,5-160,5-161,5-163,5-170,5-173,5-174,5-182,5-186,5-189,5-189(+),5-195,5-197,5-203,5-205,5-208,5-210,5-212,5-214,5-216,5-219,5-219(+),5-220,5-226,5-230˜5-232,5-234˜5-236,5-239,5-240,5-242,5-243,5-245,5-246,5-251,5-254,5-257,5-258,5-261,5-262,5-264,5-265,5-273˜5-275,5-279,5-280,5-285,5-286,5-288,5-294,5-295,5-305˜5-310,5-313,5-315,5-323,5-330,5-335,5-339,5-341,5-344,5-353˜5-360,5-374˜5-377,5-379˜5-388,5-390,5-392,5-393,5-396,5-398˜5-401,5-405,5-410,5-412,5-413,5-419,5-421˜5-423,5-426,5-427,5-429,5-432,5-433,5-440,5-453,5-455,5-460,5-461,5-463˜5-465,5-467,5-470,5-472˜5-476,5-482,5-483,5-487,5-490˜5-492,5-494˜5-496,5-498,5-499,5-501,5-510˜5-512,5-515,5-519,5-521,5-523,5-525,5-527˜5-530,5-532,5-537˜5-539,5-541,5-541(S),5-546,5-547,5-550˜5-554,5-560,5-568,5-570,5-572˜5-576,5-579,5-583,5-585,5-586,5-588,5-608,5-614,5-617,5-619,5-621,5-627,5-628,5-636,5-637,5-642,5-646,5-648,5-651,5-654,5-656,5-657,5-660,5-662,5-664,5-670,5-672,5-674,5-684,5-686,6-001,6-003,6-007,6-015˜6-023,6-027-6-045,6-048˜6-050,6-056,6-058˜6-065,6-076˜6-080,6-080(+),6-080(−),6-081˜6-083,6-086,6-090˜6-093,6-096,6-098,6-100˜6-103,6-105,6-114,6-115,6-117,6-124,6-125,6-130˜6-132,7-001˜7-004,7-006,7-008,7-009,8-003,9-009,11-039,11-041,11-054,11-098,11-101,11-132.

Test Example 11 Insecticidal Test Against Bemisia argentifolii

A wet filter paper was laid in a styrol cup having an inner diameter of7 cm, a leaf of a tomato cut out on which Bemisia argentifolii laid eggs(10-egg/leaf) was laid thereon. A 10% emulsifiable concentrate(depending on the compounds, 10% wettable powder was applied for thetest) of the compound of the present invention was diluted with watercontaining a spreading agent to prepare a chemical solution with aconcentration of 500 ppm. The chemical solution was sprayed with arotating spray tower in an amount of 2.5 ml per styrol cup, and thestyrol cups were covered with lids and contained at a thermostat chamberat 25° C. A number of dead insect(s) after 6 days was counted and a rateof dead insects was calculated by the calculation equation similar tothat in Test Example 1. Incidentally, the test was carried out with twodistricts.

As a result, the following compounds showed an insecticidal rate of 80%or more among the compounds tested.The compounds of the present invention: No.1-011,1-182,2-024*,2-025*,2-026*,2-028*,2-029*,2-033,2-034*,2-035*,2-037*,2-044*,2-047,2-050,2-051,2-058˜2-062,2-065,2-066,3-068,3-079,3-090,3-112,3-125,3-151,4-003,4-006,5-001,5-003,5-005,5-007,5-009,5-011,5-013˜5-015,5-021˜5-023,5-029,5-035,5-037˜5-041,5-045˜5-053,5-057˜5-061,5-063,5-065,5-067˜5-075,5-075(+),5-076˜5-078,5-079*,5-081,5-084˜5-089,5-090*,5-091˜5-094,5-099˜5-104,5-112˜5-114,5-117,5-118,5-120*,5-122,5-123,5-126,5-128,5-130,5-137˜5-142,5-143*,5-144,5-145,5-146*,5-148,5-151,5-151(+),5-153*,5-154,5-156,5-158˜5-160,5-161*,5-162,5-164,5-165,5-167*,5-171,5-180,5-182˜5-188,5-189(+),5-191,5-193,5-201,5-202,5-205˜5-207,5-208*,5-209˜5-216,5-218,5-219,5-219(+),5-220˜5-223,5-225˜5-234,5-236,5-238˜5-242,5-245˜5-247,5-249,5-254,5-258*,5-261,5-264,5-273˜5-275,5-277˜5-279,5-281,5-285˜5-288,5-291,5-292,5-294,5-295,5-297,5-299,5-301,5-306,5-309,5-310*,5-312˜5-315,5-318,5-319,5-321,5-323,5-330,5-332,5-335,5-339,5-341,5-344,5-345,5-353˜5-358,5-359*,5-360,5-362,5-374,5-375,5-378,5-379*,5-380*,5-381*,5-383,5-384,5-385*,5-387˜5-393,5-396*,5-397˜5-401,5-405,5-409,5-410,5-412,5-417,5-418,5-421˜5-423,5-426˜5-428,5-430,5-433,5-434,5-440,5-446,5-453,5-455,5-458,5-460,5-461,5-463˜5-465,5-468˜5-488,5-490˜5-498,5-509,5-510,5-515,5-516,5-519,5-521˜5-523,5-525,5-527˜5-532,5-538,5-539,5-541,5-543,5-549,5-551˜5-555,5-557,5-558,5-560,5-562,5-569˜5-576,5-579,5-583˜5-589,5-600,5-604˜5-607,5-611,5-612,5-616˜5-619,5-623,5-628,5-630,5-631,5-637˜5-639,5-642,5-646˜5-648,5-650˜5-657,5-660˜5-662,5-664,5-665,5-667,5-668,5-671,5-672,5-674,5-684˜5-686,6-001,6-003,6-009,6-011˜6-013,6-016˜6-018,6-020,6-021,6-022*,6-027,6-028,6-031˜6-041,6-043,6-044,6-048˜6-050,6-056,6-074˜6-076,6-078,6-079,6-081,6-083,6-089,6-090,6-093,6-095,6-096,6-098,6-100,6-102,6-110,6-114,6-124,6-130˜6-132,7-001,7-003˜7-006,7-008˜7-010,11-017,11-024,11-026,11-028,11-056,11-099,11-120,11-125,11-132.In the interim, the indication of “*” shows that the insecticidal testwas carried out by use of a chemical solution of a concentration of 100ppm.

Test Example 12 Insecticidal Test Against Green Peach Aphid

A wet cotton wool was laid in a laboratory dish having an inner diameterof 3 cm, a leaf of a cabbage cut out so as to have the same diameter waslaid thereon, and 4-green peach aphid (Myzus persicae) in the stage ofno-wing adult was left. After 1 day, a 10% emulsifiable concentrate(depending on the compounds, 10% wettable powder was applied for thetest) of the compound of the present invention was diluted with watercontaining a spreading agent to prepare a chemical solution with aconcentration of 500 ppm, and the chemical solution was sprayed with arotating spray tower (2.5 mg/cm²), and the laboratory dish was coveredwith lids and contained at a thermostat chamber at 25° C. A number ofdead insect(s) after 6 days was counted and a rate of dead insects wascalculated by the calculation equation similar to that in TestExample 1. Incidentally, the test was carried out with two districts.

As a result, the following compounds showed an insecticidal rate of 80%or more among the compounds tested.The compounds of the present invention:No.1-006,1-063,1-067,1-069,1-153,1-158,1-163,1-166,1-167,1-171,1-175,1-207,1-209,1-215,2-005,2-015,2-017,2-024*,2-025*,2-026*,2-027,2-029*,2-034*,2-044*,2-046*,2-050,2-051,2-057˜2-059,2-062,2-065,2-066,3-006,3-029,3-064,3-068,3-089,3-110,3-114,3-125,3-131,3-139,3-143,4-003,5-001,5-003,5-005,5-009,5-013,5-015,5-022,5-023,5-037˜5-041,5-045˜5-050,5-052,5-053,5-056,5-058˜5-061,5-063,5-065˜5-068,5-070˜5-075,5-075(+),5-076,5-077,5-079*,5-081,5-083˜5-086,5-090*,5-091˜5-094,5-099,5-100,5-102,5-103,5-113,5-117,5-118,5-128,5-130,5-134,5-138˜5-142,5-143*,5-144,5-145,5-146*,5-147,5-148,5-151,5-151(+),5-153*,5-154,5-156,5-158,5-160,5-161*,5-162,5-165,5-180˜5-187,5-189(+),5-193,5-202,5-205,5-209,5-210,5-212,5-214˜5-216,5-219,5-219(+),5-220˜5-223,5-226,5-228,5-230,5-231,5-233,5-234,5-236,5-238,5-240,5-242,5-243*,5-245˜5-247,5-251,5-254,5-256,5-258*,5-259,5-261,5-264,5-272˜5-275,5-277˜5-280,5-282,5-284˜5-288,5-291,5-294,5-295,5-300,5-301,5-306,5-307,5-309,5-310*,5-313˜5-315,5-320,5-321,5-323,5-330,5-334,5-335,5-339,5-341,5-343,5-344,5-348,5-352,5-353˜5-358,5-359*,5-360,5-362,5-364,5-374,5-375,5-378,5-379*,5-380*,5-383,5-384,5-385*,5-387,5-389,5-390,5-392,5-393,5-398,5-399,5-401,5-409,5-410,5-415,5-418,5-421˜5-424,5-427,5-428,5-433,5-434,5-440˜5-442,5-446,5-453,5-455,5-458˜5-465,5-468,5-470˜5-484,5-486,5-487,5-490,5-491,5-494˜5-499,5-510,5-512,5-515,5-516,5-519,5-523,5-527˜5-529,5-532,5-538,5-541,5-541(S),5-546,5-551˜5-554,5-557,5-558,5-560,5-569˜5-576,5-581,5-583,5-587,5-588,5-608,5-611,5-612,5-617,5-619,5-628,5-630˜5-632,5-637,5-638,5-642,5-644,5-646,5-654,5-655,5-662,5-664,5-669,5-670,5-672,5-674,5-684,5-686,6-001,6-003,6-005*,6-007,6-009˜6-012,6-015*,6-016˜6-021,6-022*,6-027,6-028,6-030˜6-033,6-035˜6-044,6-048˜6-050,6-054,6-056˜6-059,6-063,6-066,6-074˜6-076,6-078˜6-084,6-086,6-089˜6-095,6-097,6-098,6-100˜6-103,6-112,6-114,6-115,6-121,6-124,6-130˜6-132,7-003˜7-007,7-009,8-005,8-006,9-004,9-009,10-002,10-006,11-005,11-006,11-026,11-118,11-125,11-130,12-004.In the interim, the indication of “*” shows that the insecticidal testwas carried out by use of a chemical solution of a concentration of 100ppm.

Test Example 13 Insecticidal Test Against Japanese Mealybug

A wet filter paper was laid in a styrol cup having an inner diameter of7 cm, a leaf of a common bean cut out so as to have the same diameterwas laid thereon, and 10-Japanese mealybug (Planococcus kraunhiae) inthe first instar larva per leaf was inoculated thereon. A 10%emulsifiable concentrate (depending on the compounds, 10% wettablepowder was applied for the test) of the compound of the presentinvention was diluted with water containing a spreading agent to preparea chemical solution with a concentration of 500 ppm. The chemicalsolution was sprayed with a rotating spray tower in an amount of 2.5 mlper styrol cup, and the styrol cups were covered with lids and containedat a thermostat chamber at 25° C. A number of dead insect(s) after 6days was counted and a rate of dead insects was calculated by thecalculation equation similar to that in Test Example 1. Incidentally,the test was carried out with two districts.

As a result, the following compounds showed an insecticidal rate of 80%or more among the compounds tested.The compounds of the present invention: No.1-011,1-177,1-182,2-020,2-028*,2-029*,2-033,2-034*,2-035*,2-037*,2-039*,2-040*,2-041*,2-042*,2-044*,2-045*,2-046*,2-047,2-048*,2-049*,2-050˜2-052,2-055*,2-057,2-059,2-062,2-065˜2-067,3-065,3-069,3-085,3-086,3-091˜3-093,3-104,3-109,3-125,3-151,4-003,4-004,4-006,5-001,5-003,5-005,5-007,5-009,5-013˜5-015,5-017,5-022,5-023,5-029,5-037,5-039˜5-041,5-045˜5-050,5-052,5-053,5-057˜5-061,5-063˜5-065,5-067˜5-075,5-075(+),5-076˜5-078,5-081,5-083˜5-089,5-090*,5-091˜5-094,5-098˜5-105,5-109,5-111˜5-114,5-116˜5-118,5-121,5-123,5-126,5-128,5-129*,5-130,5-131*,5-138˜5-142,5-143*,5-144,5-145,5-146*,5-147,5-148,5-151,5-151(+),5-153*,5-154,5-156,5-158˜5-160,5-161*,5-162,5-164,5-165,5-166,5-167*,5-168*,5-171,5-172*,5-179˜5-188,5-189(+),5-190(+),5-192˜5-194,5-201,5-202,5-205,5-206,5-208*,5-210˜5-212,5-214˜5-216,5-219,5-219(+),5-221,5-222,5-223,5-226˜5-234,5-236˜5-240,5-242,5-245˜5-247,5-249,5-251,5-253,5-254,5-255*,5-256,5-257,5-258*,5-259,5-261,5-264,5-269*,5-271*,5-272˜5-288,5-291,5-292,5-295˜5-297,5-299˜5-301,5-302*,5-303,5-306,5-307,5-309,5-310*,5-312˜5-315,5-318,5-319,5-321,5-322,5-323,5-331,5-332,5-334˜5-336,5-338,5-339,5-344,5-345,5-348,5-349,5-353˜5-358,5-360˜5-362,5-375,5-378,5-379*,5-380*,5-381*,5-383,5-384,5-385*,5-387,5-388,5-390,5-392,5-393,5-395,5-396*,5-397˜5-399,5-401,5-406,5-407,5-410,5-412,5-417˜5-419,5-422˜5-424,5-426˜5-434,5-439˜5-443,5-445,5-446,5-452,5-453,5-457,5-458,5-460,5-461,5-463˜5-465,5-468,5-470˜5-473,5-475˜5-477,5-480,5-482˜5-485,5-487,5-488,5-490˜5-492,5-494˜5-496,5-498,5-500,5-516,5-519,5-521˜5-523,5-525,5-527,5-531,5-532,5-538,5-541,5-543,5-546,5-547,5-549˜5-554,5-558,5-569,5-572˜5-576,5-579,5-581˜5-584,5-587,5-589,5-599,5-605,5-607,5-616,5-623,5-627,5-628,5-637,5-638,5-647,5-651,5-654˜5-656,5-658˜5-662,5-664˜5-666,5-668˜5-672,5-674,5-684˜5-686,6-001˜6-003,6-005*,6-006*,6-007˜6-013,6-015*,6-016˜6-021,6-022*,6-023,6-024*,6-025*,6-026˜6-050,6-054˜6-056,6-058,6-059,6-063,6-066,6-074˜6-076,6-078˜6-080,6-080(+),6-082˜6-085,6-089,6-090˜6-096,6-098˜6-102,6-103,6-110,6-114,6-115,6-130˜6-132,7-003˜7-010,8-003,9-003,9-011,10-002,10-006,11-024˜11-026,11-043,11-045,11-056,11-058,11-059,11-089,11-120,11-125,11-132,12-006,12-008.In the interim, the indication of “*” shows that the insecticidal testwas carried out by use of a chemical solution of a concentration of 100ppm.

Test Example 14 Insecticidal Test Against Cucurbit Leaf Beetle

A 10% emulsifiable concentrate (depending on the compounds, 10% wettablepowder was applied for the test) of the compound of the presentinvention was diluted with water containing a spreading agent to preparea chemical solution with a concentration of 500 ppm. To the chemicalsolution was dipped leaves of cucumber for about 10 seconds, and afterair-drying, they were placed in a laboratory dish, then 5-cucurbit leafbeetle (Aulacophora femoralis) in the stage of second instar larva perthe dish were released therein, and the dish was covered with a lid andcontained at a thermostat chamber at 25° C. A number of dead insect(s)after 6 days was counted and a rate of dead insects was calculated bythe calculation equation similar to that in Test Example 1.Incidentally, the test was carried out with two districts.

As a result, the following compounds showed an insecticidal rate of 80%or more among the compounds tested.The compounds of the present invention: No.1-005,1-015,1-016,1-040,1-042,1-055˜1-057,1-059,1-061˜1-067,1-069˜1-071,1-073,1-074,1-076,1-077,1-079˜1-081,1-083˜1-085,1-087,1-088,1-090,1-092˜1-095,1-098,1-099,1-102,1-104˜1-110,1-113,1-116,1-118,1-119,1-122˜1-129,1-131,1-135,1-136,1-138,1-146,1-147,1-151˜1-153,1-155˜1-157,1-159,1-166,1-167,1-171,1-172,1-174˜1-177,1-179˜1-185,1-187˜1-189,1-194,1-199,1-206,1-207,1-210,1-212,1-214,1-215,1-220,1-225,2-001,2-004,2-006,2-011,2-013,2-019˜2-022,2-025˜2-029,2-031,2-032,2-034˜2-055,2-057˜2-068,3-002,3-003,3-006,3-011,3-018,3-025˜3-028,3-031˜3-035,3-037,3-044,3-046,3-047,3-050,3-058,3-061˜3-065,3-068˜3-072,3-074,3-076,3-078˜3-081,3-084˜3-087,3-089˜3-095,3-097˜3-116,3-118˜3-125,3-127˜3-132,3-134˜3-136,3-138˜3-143,3-145˜3-151,4-003˜4-007,4-009˜4-011,5-001˜5-015,5-017,5-021˜5-023,5-028˜5-042,5-044˜5-075,5-075(+),5-075(−),5-076˜5-081,5-083˜5-095,5-097,5-099˜5-107,5-109˜5-130,5-132˜5-135,5-137˜5-151,5-151(+),5-151(−),5-152˜5-156,5-158˜5-189,5-189(+),5-190(+),5-191˜5-219,5-219(+),5-219(−),5-220˜5-236,5-238˜5-296,5-298˜5-326,5-329˜5-339,5-341˜5-350,5-352˜5-363,5-365,5-369,5-371,5-374˜5-403,5-405˜5-413,5-415˜5-447,5-449,5-452˜5-455,5-458˜5-491,5-493˜5-503,5-505,5-507˜5-534,5-536˜5-540,5-540(+),5-541,5-541(R),5-541(S),5-542˜5-560,5-562˜5-570,5-572˜5-590,5-592˜5-602,5-604˜5-609,5-611˜5-619,5-621˜5-648,5-650,5-651,5-653˜5-672,5-674,5-676,5-678,5-684˜5-686,6-001˜6-013,6-015˜6-024,6-026˜6-051,6-053˜6-067,6-070,6-071,6-074˜6-080,6-080(46-080(−),6-081˜6-086,6-089˜6-096,6-098˜6-106,6-108˜6-115,6-117˜6-127,6-129˜6-133,7-001˜7-010,8-001˜8-007,9-003,9-009,9-010,10-002˜10-005,11-005,11-015,11-017,11-020,11-023˜11-026,11-038,11-043,11-045,11-046,11-052˜11-054,11-056˜11-060,11-066,11-067,11-072,11-076,11-098,11-099,11-101˜11-104,11-106,11-108,11-110,11-112˜11-114,11-119,11-120,11-124,11-125,11-129,11-130,11-132,12-006.

Test Example 15 Insecticidal Test Against Serpentine Leaf Miner

A 10% emulsifiable concentrate (depending on the compounds, 10% wettablepowder was applied for the test) of the compound of the presentinvention was diluted with water containing a spreading agent to preparea chemical solution with a concentration of 500 ppm. To the chemicalsolution was dipped leaves of common bean on which serpentine leaf miner(Liriomyza trifolii) laid eggs (10 eggs/leaf) for about 10 seconds, andafter air-drying, they were placed on a wet filter paper laid in astyrol cup having an inner diameter of 7 cm, and the styrol cup wascovered with a lid and contained at a thermostat chamber at 25° C. Anumber of dead insect(s) after 6 days was counted and a rate of deadinsects was calculated by the calculation equation similar to that inTest Example 1. Incidentally, the test was carried out with twodistricts.

As a result, the following compounds showed an insecticidal rate of 80%or more among the compounds tested.The compounds of the present invention: No.1-175,1-177,2-029*,2-034*,2-035*,2-044*,2-045*,2-050,2-051,2-057,2-059,2-062,2-064,2-065,2-067,3-060,3-068,3-069,3-071,3-072*,3-085,3-086,3-093,3-105,3-109,3-112,3-125,3-148,3-151,5-001,5-003,5-005,5-007,5-009,5-015,5-022,5-023,5-036,5-037,5-040,5-041,5-045˜5-053,5-058˜5-061,5-063˜5-065,5-067,5-068,5-070˜5-075,5-075(+),5-076,5-077,5-081,5-083,5-085˜5-089,5-090*,5-091˜5-094,5-099˜5-105,5-113,5-117˜5-119,5-120*,5-121˜5-123,5-124*,5-126,5-129*,5-131*,5-133*,5-138˜5-142,5-144,5-145,5-147,5-148,5-150,5-151,5-151(+),5-154,5-156,5-158,5-160,5-161*,5-162,5-164˜5-166,5-168*,5-169,5-171,5-172*,5-178,5-180,5-182˜5-188,5-189(+),5-201,5-202,5-208*,5-209,5-210,5-212,5-214˜5-216,5-217*,5-219,5-219(+),5-221˜5-223,5-226˜5-234,5-236,5-238,5-239,5-241,5-245˜5-247,5-251,5-256,5-257,5-258*,5-259,5-261,5-264,5-265,5-270,5-274,5-275,5-283,5-284,5-286,5-291,5-294,5-295,5-302*,5-303,5-306,5-309,5-310*,5-313˜5-315,5-319,5-323,5-335,5-336,5-338,5-339,5-341,5-344,5-345,5-353˜5-358,5-360,5-362,5-374,5-375,5-378,5-379*,5-380*,5-381*,5-383,5-384,5-385*,5-387,5-388,5-390,5-392,5-393,5-395,5-396*,5-397˜5-401,5-408˜5-413,5-415,5-417˜5-423,5-425˜5-430,5-432,5-433,5-439˜5-441,5-443,5-445,5-446,5-452,5-453,5-455,5-458˜5-465,5-467,5-468,5-470˜5-488,5-490,5-491,5-494˜5-499,5-501,5-508˜5-512,5-515˜5-517,5-519,5-520˜5-523,5-527˜5-532,5-538,5-539,5-541,5-541(S),5-543,5-549,5-551˜5-554,5-556˜5-560,5-566,5-569,5-570,5-572˜5-576,5-579,5-581,5-584,5-596,5-601,5-606,5-616,5-617,5-630,5-631,5-634,5-635,5-637,5-638,5-642,5-643,5-646,5-651,5-653˜5-657,5-659,5-660,5-662,5-664˜5-672,5-674,5-684˜5-686,6-001,6-004*,6-005*,6-006*,6-007,6-008,6-011˜6-013,6-015*,6-016˜6-021,6-022*,6-024*,6-025*,6-027,6-031,6-033˜6-041,6-043,6-044,6-048˜6-050,6-054˜6-056,6-066,6-070,6-074˜6-076,6-078,6-079,6-081,6-083,6-085,6-089,6-091,6-092,6-093,6-095,6-098,6-100,6-102,6-103,6-110,6-114,6-123,6-124,6-129˜6-133,7-003,7-005˜7-009.In the interim, the indication of “*” shows that the insecticidal testwas carried out by use of a chemical solution of a concentration of 100ppm.

Test Example 16 Insecticidal Test Against Two-Spotted Spider Mite

A wet filter paper was laid in a styrol cup having an inner diameter of7 cm, a leaf of a common bean cut out so as to have the same diameterwas laid thereon, and 10 larvae of two-spotted spider mite (Tetranychusurticae) per leaf was inoculated thereon. A 10% emulsifiable concentrate(depending on the compounds, 10% wettable powder was applied for thetest) of the compound of the present invention was diluted with watercontaining a spreading agent to prepare a chemical solution with aconcentration of 500 ppm. The chemical solution was sprayed with arotating spray tower in an amount of 2.5 ml per styrol cup, and thestyrol cups were covered with lids and contained at a thermostat chamberat 25° C. A number of dead insect(s) after 6 days was counted and a rateof dead insects was calculated by the calculation equation similar tothat in Test Example 1. Incidentally, the test was carried out with twodistricts.

As a result, the following compounds showed an insecticidal rate of 80%or more among the compounds tested.The compounds of the present invention: No.1-177,1-182,2-027,2-028*,2-029*,2-034*,2-035*,2-036,2-037*,2-039*,2-040*,2-041*,2-042*,2-044*,2-045*,2-046*,2-047,2-048*,2-049*,2-050˜2-052,2-057˜2-063,2-065˜2-067,3-068,3-084,3-086,3-109,3-110,3-1,2,3-114,3-124,3-131,3-151,5-001,5-003,5-005,5-007˜5-009,5-011,5-013,5-015,5-019,5-021,5-022,5-023,5-028,5-029,5-035˜5-037,5-040,5-041,5-045-5-053,5-057˜5-075,5-075(+),5-076˜5-078,5-080˜5-089,5-090*,5-091˜5-094,5-098˜5-105,5-109,5-112˜5-114,5-117˜5-119,5-121˜5-123,5-126,5-128,5-129*,5-130,5-132,5-134,5-136˜5-142,5-143*,5-144,5-145,5-146*,5-147,5-148,5-150,5-151,5-151(+),5-152,5-153*,5-154˜5-156,5-158˜5-160,5-161*,5-162˜5-166,5-167*,5-168*,5-171,5-172*,5-177˜5-180,5-182˜5-188,5-189*,5-189(+),5-190(+),5-191,5-192,5-196*,5-197*,5-199˜5-202,5-204˜5-207,5-208*,5-209˜5-212,5-214˜5-216,5-218,5-219,5-219(+),5-219(−),5-220˜5-234,5-235*,5-236,5-238˜5-242,5-243*,5-245˜5-247,5-249,5-251,5-254,5-255*,5-256,5-257,5-258*,5-259,5-261,5-264,5-265,5-269*,5-271*,5-273˜5-275,5-277˜5-279,5-283˜5-286,5-288,5-291,5-292,5-294,5-295,5-299˜5-301,5-306,5-307,5-312˜5-316,5-321,5-323,5-325,5-330,5-336,5-338,5-339,5-341,5-344,5-345,5-349,5-353˜5-358,5-360,5-362,5-374,5-375,5-376*,5-377*,5-378,5-379*,5-380*,5-381*,5-383,5-384,5-385*,5-386*,5-387˜5-395,5-396*,5-397˜5-399,5-401,5-402,5-405,5-406,5-408˜5-413,5-415,5-417˜5-419,5-421˜5-423,5-425˜5-427,5-430,5-432,5-433,5-440,5-441,5-443,5-445,5-452˜5-455,5-457˜463,5-465,5-467,5-468,5-470˜5-487,5-489˜5-492,5-494˜5-499,5-503,5-505,5-506,5-509˜5-513,5-515˜5-525,5-527˜5-534,5-538,5-539,5-540(+),5-543˜5-545,5-548˜5-554,5-557˜5-560,5-566,5-568˜5-570,5-572˜5-576,5-578,5-579,5-581,5-583,5-584,5-600,5-601,5-604,5-606,5-616,5-617,5-630,5-631,5-635,5-637,5-638,5-642,5-646,5-647,5-650,5-651,5-654˜5-657,5-659˜5-662,5-664˜5-672,5-678,5-684˜5-686,6-001,6-003,6-007,6-008,6-011˜6-013,6-015*,6-016˜6-021,6-023,6-027,6-030˜6-044,6-046˜6-050,6-054˜6-056,6-066,6-074˜6-076,6-078,6-079,6-082˜6-085,6-089˜6-093,6-095,6-096,6-098,6-100,6-102,6-103,6-110,6-112,6-114,6-115,6-121,6-123,6-124,6-129˜6-133,7-003˜7-010,8-003,10-002,10-006,11-026,11-098,11-108,12-002.In the interim, the indication of “*” shows that the insecticidal testwas carried out by use of a chemical solution of a concentration of 100ppm.

Test Example 17 Insecticidal Test Against Pink Citrus Rust Mite

A wet filter paper was laid in a styrol cup having an inner diameter of7 cm, a leaf of a mandarin orange cut out so as to have the samediameter was laid thereon, and 10 larvae of pink citrus rust mite(Aculops pelekassi) per leaf was inoculated thereon. A 10% emulsifiableconcentrate (depending on the compounds, 10% wettable powder was appliedfor the test) of the compound of the present invention was diluted withwater containing a spreading agent to prepare a chemical solution with aconcentration of 100 ppm. The chemical solution was sprayed with arotating spray tower in an amount of 2.5 ml per styrol cup, and thestyrol cups were covered with lids and contained at a thermostat chamberat 25° C. A number of dead insect(s) after 6 days was counted and a rateof dead insects was calculated by the calculation equation similar tothat in Test Example 1. Incidentally, the test was carried out with twodistricts.

As a result, the following compounds showed an insecticidal rate of 80%or more among the compounds tested.The compounds of the present invention: No.1-177,3-093,3-112,5-001˜5-003,5-005,5-008,5-009,5-022,5-023,5-036,5-037,5-040,5-041,5-046,5-047,5-049,5-050,5-053,5-057˜5-059,5-061,5-063,5-065,5-066,5-069˜5-071,5-074˜5-077,5-081,5-083,5-084,5-086,5-088,5-111˜5-113,5-121,5-137˜5-140,5-148,5-151,5-174,5-182,5-183,5-185,5-187,5-188,5-202,5-205,5-206,5-215,5-216,5-219˜5-221,5-225,5-226,5-233˜5-235,5-241,5-247,5-274,5-285,5-291,5-294,5-295,5-301,5-313,5-323,5-331,5-334,5-338,5-339,5-355,5-360,5-374,5-378,5-387˜5-390,5-393,5-397,5-398,5-480,5-494,5-638,5-642,5-645,6-003,6-017,6-020,6-021,6-027,6-031,6-033˜6-035,6-043,6-049,6-054,6-064,6-070,6-076,6-131,7-003,7-007˜7-009,10-002.

Test Example 18 Insecticidal Test Against Broad Mite

A wet filter paper was laid in a styrol cup having an inner diameter of7 cm, a leaf of a common bean cut out so as to have the same diameterwas laid thereon, and 10 adults of broad mite (Polyphagotarsonemuslatus) per leaf was inoculated thereon. A 10% emulsifiable concentrate(depending on the compounds, 10% wettable powder was applied for thetest) of the compound of the present invention was diluted with watercontaining a spreading agent to prepare a chemical solution with aconcentration of 100 ppm. The chemical solution was sprayed with arotating spray tower in an amount of 2.5 ml per styrol cup, and thestyrol cups were covered with lids and contained at a thermostat chamberat 25° C. A number of dead insect(s) after 2 days was counted and a rateof dead insects was calculated by the calculation equation similar tothat in Test Example 1. Incidentally, the test was carried out with twodistricts.

As a result, the following compounds showed an insecticidal rate of 80%or more among the compounds tested.The compounds of the present invention:No.3-093,5-009,5-036,5-037,5-040,5-041,5-050,5-053,5-058,5-063,5-067,5-071,5-075˜5-077,5-083,5-088,5-089,5-113,5-121,5-140,5-147,5-148,5-151,5-174,5-179,5-185,5-188,5-214,5-215,5-219,5-230,5-233˜5-236,5-249,5-251,5-254,5-274,5-288,5-289,5-291,5-294,5-309,5-332,5-339,5-355,5-360,5-374,5-375,5-387,5-398,5-474,5-476,5-480,5-494,5-604,5-642,6-017,6-026,6-031,6-033˜6-035,6-038,6-045,6-064,6-070,6-076,6-131,7-003,7-007˜7-009.

Test Example 19 Insecticidal Test Against Ctenocephalides felis

After 400 l of acetone solution in which 4 mg of the compound of thepresent invention was dissolved in 40 ml of acetone (concentration 100ppm) was coated on the bottom face and side face of a laboratory dishhaving an inner diameter of 5.3 cm, acetone was vaporized to prepare athin film of the compound of the present invention on the inner wall ofthe laboratory dish. As the surface area of the inner wall is 40 cm²,the treated dosage is 1 g/cm². 10 adults of Ctenocephalides felis (maleand female are mixed) were left in the laboratory dish, covered with lidand contained at a thermostat chamber at 25° C. A number of deadinsect(s) after 4 days was counted and a rate of dead insects wascalculated by the calculation equation similar to that in TestExample 1. Incidentally, the test was carried out with one district.

As a result, the following compounds showed an insecticidal rate of 80%or more among the compounds tested.The compounds of the present invention: No.2-029*,2-052,3-151,5-002,5-003,5-005,5-007,5-008,5-012,5-013,5-023,5-029,5-037,5-058,5-071*,5-072,5-075*,5-076*,5-077,5-086,5-088*,5-093*,5-100*,5-101*,5-111*,5-117,5-121,5-130*,5-138,5-139,5-140*,5-142*,5-148*,5-151*,5-160*,5-161*,5-165*,5-174*,5-182*,5-184,5-187,5-188,5-192,5-205,5-206,5-209,5-214*,5-215*,5-218,5-219*,5-223,5-229,5-230,5-232,5-234*,5-235*,5-236,5-238,5-240,5-241*,5-243*,5-245*,5-247,5-264,5-274*,5-287,5-291,5-294,5-310*,5-312,5-313,5-323,5-354*,5-356*,5-359*,5-360,5-362,5-376*,5-377*,5-378*,5-379*,5-383*,5-384*,5-387*,5-389*,5-390,5-393,5-399*,5-401*,5-405*,5-412*,5-423*,5-427*,5-429*,5-430*,5-440*,5-461*,5-466*,5-468*,5-470*,5-473,5-474*,5-475,5-476,5-477*,5-478*,5-480*,5-487,5-494*,5-495-5-499,5-579*,5-587*,5-623,5-646*,5-648*,5-658,6-020,6-026,6-033,6-034*,6-035*,6-043*,6-046˜6-049,6-054,6-055,6-064*,6-065*,6-074,6-092,6-094,6-095,6-129,6-130,6-133,7-002*,7-004,7-008*,7-009.In the interim, the indication of “*” shows that the insecticidal testwas carried out with a treated dosage of 0.1 g/cm².

Test Example 20 Insecticidal Test Against American Dog Tick

After 400 l of acetone solution in which 4 mg of the compound of thepresent invention was dissolved in 40 ml of acetone (concentration 100ppm) was coated on the bottom face and side face of two laboratorydishes having an inner diameter of 5.3 cm, acetone was vaporized toprepare a thin film of the compound of the present invention on theinner wall of the laboratory dish. As the surface area of the inner wallis 40 cm², the treated dosage is 1 g/cm². 10-American dog tick(Dermacentor variabilis) (male and female are mixed) in the stage ofprotonymph were left in the laboratory dishes, two laboratory dishestogether were sealed with a tape so that ticks do not escape, andcontained at a thermostat chamber at 25° C. A number of dead insect(s)after 4 days was counted and a rate of dead insects was calculated bythe calculation equation similar to that in Test Example 1.Incidentally, the test was carried out with one district.

As a result, the following compounds showed an insecticidal rate of 80%or more among the compounds tested.The compounds of the present invention: No.2-029*,2-052,2-054*,5-003,5-005,5-008,5-023,5-029,5-037,5-058,5-063*,5-071*,5-072,5-075*,5-076*,5-077,5-086,5-088*,5-093*,5-100*,5-101*,5-117,5-121,5-128,5-130*,5-138,5-139,5-140*,5-142*,5-148*,5-151*,5-160*,5-161*,5-165*,5-174*,5-182*,5-184,5-187,5-188,5-191,5-192,5-205,5-206,5-209,5-214*,5-215*,5-219*,5-223,5-229,5-230,5-232,5-233*,5-234*,5-235*,5-236,5-238,5-240,5-241*,5-243*,5-245*,5-247,5-264,5-274*,5-287,5-291,5-294,5-308*,5-309*,5-310*,5-312,5-313,5-320,5-321,5-323,5-354*,5-356*,5-359*,5-360,5-362,5-376*,5-377*,5-378*,5-379*,5-383*,5-384*,5-386*,5-387*,5-390,5-393,5-399*,5-401*,5-405*,5-412*,5-418*,5-423*,5-427*,5-429*,5-430*,5-432*,5-440*,5-461*,5-466*,5-468*,5-469*,5-470*,5-473*,5-474*,5-475*,5-476*,5-477*,5-478*,5-480*,5-487*,5-494*,5-495*,5-496*,5-497*,5-498*,5-499*,5-500*,5-555*,5-579*,5-581*,5-585*,5-587*,5-588*,5-589*,5-593*,5-601*,5-607*,5-610*,5-623*,5-638*,5-646*,5-648*,5-654*,5-658*,6-020,6-026,6-033,6-034*,6-035*,6-043*,6-046˜6-049,6-054,6-055,6-064*,6-065*,6-074,6-092*,6-094*,6-095*,6-129*,6-130*,6-133*,7-004,7-008*,7-009,11-056.In the interim, the indication of “*” shows that the insecticidal testwas carried out with a treated dosage of 0.1 g/cm².

Test Example 21 Insecticidal Test Against German Cockroach

A chemical solution having a concentration of 10 g/l was prepared bydiluting the compound of the present invention with acetone. Thechemical solution was coated on the abdominal region of male adults ofGerman cockroach (Blattella germanica) in an amount of 1 l percockroach, and the treated cockroaches were contained at a thermostatchamber at 25° C. A number of dead insect(s) after 2 days was countedand a rate of dead insects was calculated by the calculation equationsimilar to that in Test Example 1. Incidentally, the test was carriedout with five districts.

As a result, the following compounds showed an insecticidal rate of 80%or more among the compounds tested.The compounds of the present invention: No.5-075,5-140*,5-147*,5-148*,5-151*,5-174*,5-234*,5-412*,5-480*,5-494*,5-541*,5-638*,6-103*.

Test Example 22 Insecticidal Test Against Musca domestica

A chemical solution having a concentration of 1 g/l was prepared bydiluting the compound of the present invention with acetone. Thechemical solution was coated on the abdominal region of female adults ofMusca domestica in an amount of 1 l per fly, and the treated flies werecontained at a thermostat chamber at 25° C. A number of dead insect(s)after 2 days was counted and a rate of dead insects was calculated bythe calculation equation similar to that in Test Example 1.Incidentally, the test was carried out with ten districts.

As a result, the following compounds showed an insecticidal rate of 80%or more among the compounds tested.The compounds of the present invention:

No.5-075,5-140,5-147,5-148,5-151,5-174,5-219,5-234,5-412,5-480,5-494,5-541,5-638,6-103.Test Example 23 Insecticidal Test Against Eastern Subterranean Termite

A 10% emulsifiable concentrate (depending on the compounds, 10% wettablepowder was applied for the test) of the compound of the presentinvention was diluted with water containing a spreading agent to preparea chemical solution with a concentration of 10 ppm. 0.5 ml of thechemical solution was added dropwise in 10 g of sand and mixed. A filterpaper and the sand treated with the chemical solution were placed in alaboratory dish in which 1% agar was laid. 10-Eastern subterraneantermite (Reticulitermes flavipes) per dish was left and contained at athermostat chamber at 25° C. A number of dead insect(s) after 2 days wascounted and a rate of dead insects was calculated by the calculationequation similar to that in Test Example 1.

As a result, the following compounds showed an insecticidal rate of 80%or more among the compounds tested.The compounds of the present invention: No. 5-234.

Test Example 24 Insecticidal Test Against Rust-Red Flour Beetle

A chemical solution having a concentration of 0.1 mg/ml was prepared bydiluting the compound of the present invention with acetone. After 10 mlof the chemical solution was added dropwise in 10 g of bran, 20 adultsof rust-red flour beetle (Tribolium castaneum) were left therein, andcontained at a thermostat chamber at 25° C. A number of dead insect(s)after 2 months was counted and a rate of dead insects was calculated bythe calculation equation similar to that in Test Example 1.Incidentally, the test was carried out with two districts.

As a result, the following compounds showed an insecticidal rate of 80%or more among the compounds tested.The compounds of the present invention: No. 5-234.

INDUSTRIAL APPLICABILITY

The isoxazoline-substituted benzanilide compounds according to thepresent invention are extremely useful compounds showing an excellentpesticidal activity, particularly an insecticidal and acaricidalactivity, and causing little adverse effect against non-targeted beingssuch as mammals, fishes and useful insects.

LENGTHY TABLES The patent application contains a lengthy table section.A copy of the table is available in electronic form from the USPTO website(http://seqdata.uspto.gov/?pageRequest=docDetail&DocID=US20110251398A1).An electronic copy of the table will also be available from the USPTOupon request and payment of the fee set forth in 37 CFR 1.19(b)(3).

1. A 3,5-Bis (substituted aryl) substituted isoxazoline compound offormula (2) or a salt thereof:

wherein A¹ is a carbon atom or nitrogen atom; X¹ is selected from thegroup consisting of a halogen atom, —SF₅, C₁-C₆haloalkyl, hydroxyC₁-C₆haloalkyl, C₁-C₆alkoxy C₁-C₆haloalkyl, C₁-C₆haloalkoxyC₁-C₆haloalkyl, C₃-C₈halocycloalkyl, C₁-C₆haloalkoxy, C₁-C₃haloalkoxyC₁-C₃haloalkoxy, C₁-C₆haloalkylthio, C₁-C₆haloalkylsulfinyl andC₁-C₆haloalkylsulfonyl; X² is selected from the group consisting of ahalogen atom, cyano, nitro, C₁-C₆alkyl, C₁-C₆haloalkyl, —OR⁵, —OSO₂R⁵and —S(O)_(r)R⁵, wherein, when m1 is 2, each X² may be identical with ordifferent from each other; Y is selected from the group consisting of ahalogen atom, cyano, nitro, C₁-C₄alkyl, C₁-C₄haloalkyl, C₁-C₄alkoxy,C₁-C₄haloalkoxy, C₁-C₆alkylthio, C₁-C₆haloalkylthio, C₁-C₆alkylsulfonyl,C₁-C₆haloalkylsulfonyl, —NHR⁷ and —N(R⁷)R⁶; R³ is C₁-C₆haloalkyl orC₃-C₈halocycloalkyl; R⁵ is C₁-C₆alkyl or C₁-C₆haloalkyl; R⁶ is selectedfrom the group consisting of C₁-C₆alkyl, —CHO, C₁-C₆alkylcarbonyl,C₁-C₆haloalkylcarbonyl, C₁-C₆alkoxycarbonyl, C₁-C₆alkylthiocarbonyl,C₁-C₆alkoxythiocarbonyl, C₁-C₆alkyldithiocarbonyl, C₁-C₆alkylsulfonyl orC₁-C₆haloalkylsulfonyl, R7 is hydrogen atom and C1-C6alkyl; R isselected from the group consisting of a halogen atom, cyano, nitro,—NH2, halosulfonyloxy, C1-C6alkylsulfonyloxy, C1-C6haloalkylsulfonyloxy,phenylsulfonyloxy, phenylsulfonyloxy substituted with (Z)_(p1) and—C(O)R^(a); R^(a) is selected from the group consisting of a halogenatom, —OH, C₁-C₆alkoxy, 1-pyrazolyl, 1-imidazolyl and 1-triazolyl; Z isselected from the group consisting of a halogen atom, C₁-C₆alkyl andC₁-C₆haloalkyl, wherein when p1 is an integer of 2 or more, each Z maybe identical with or different from each other; m1 is an integer of 0 to2; n is an integer of 0 or 1; p1 is an integer of 1 to 5; and r is aninteger of 0 to
 2. 2. A pesticide comprising the 3,5-Bis (substitutedaryl) substituted isoxazoline compound of formula 2 or the salt thereofaccording to claim
 1. 3. An agrochemical comprising the 3,5-Bis(substituted aryl) substituted isoxazoline compound of formula 2 or thesalt thereof according to claim
 1. 4. An endo- or ecto-parasiticide formammals or birds comprising the 3,5-Bis (substituted aryl) substitutedisoxazoline compound of formula 2 or the salt thereof according toclaim
 1. 5. An insecticide or acaricide comprising the 3,5-Bis(substituted aryl) substituted isoxazoline compound of formula 2 or thesalt thereof according to claim 1.